The first total synthesis of (−)-sinulariol-B and three other cembranoids

The first total synthesis of (−)-sinulariol-B, a marine cembrandiol, was achieved from geraniol. Three other cembranoids were also synthesized from (−)-sinulariol-B.     

Total synthesis of Carpatamides A–D

A synthetic strategy was developed for the synthesis of the common core structure of Carpatamides A–D. The total synthesis of Carpatamides A and C was completed in 6 steps and of Carpatamides B and D in 7 steps, by employing the Wittig olefination, olefin cross metathesis and acid amine coupling reactions as key steps.     

A concise total synthesis of (±)-trigonoliimine B

Trigonoliimine B, a hexacyclic alkaloid, is synthesized in seven steps from simple starting materials. The synthesis features the use of an α-isocyanoacetate as a glycine template for the preparation of an α,α-disubstituted α-amino ester that is appropriately functionalized for the construction of C, D, and E rings. Sulfolane was found to be the solvent of choice for the unprecedented Bischler-Napieralski reaction implemented for the construction of a seven-membered ring with concurrent formation of an exo-imine function.     

A total synthesis of (+)-preussin and its 5-epimer

(+)-Preussin (1) and its 5-epimer were synthesized from the divmylcarbmol (3) with Sharpless asymmetric epoxidation of 3 and the oxidative cyclization of 9 with PDC as the key steps     

First total synthesis of the β-carboline alkaloids trigonostemine A,trigonostemine B and a new synthesis of pityriacitrin and hyrtiosulawesine

The total synthesis of four natural products, trigonostemine A, trigonostemine B, pityriacitrin, and hyrtiosulawesine was accomplished. The key intermediates, variously substituted 1-formyl-β-carbolines, were prepared in five steps via a novel synthetic approach using readily available starting materials. These formyl derivatives were then further transformed, providing a general route for the synthesis of the four title alkaloids. The method reported herein represents the first total synthesis of the two trigonostemines and a new pathway to pityriacitrin and hyrtiosulawesine.     

First total synthesis of (−)-aplyolide A

The first total synthesis of (−)-aplyolide A², (16S)-methyloxacyclohexadeca-(5Z,8Z,11Z,14Z)-tetraen-2-one, 1 is reported. The synthesis is based on three consecutive couplings of terminal alkynes with propargylic halides and proves the absolute configuration of the stereogenic center of the natural product.     

A concise total synthesis of (±)- and (-)-okilactomycin D

The spirotetronate okilactomycin D (7) has been efficiently synthesized by a route featuring a substrate-controlled, diastereoselective (8:1) intramolecular Diels-Alder (IMDA) reaction of 11. The assigned absolute configuration of (-)-7 was confirmed.     

A versatile enantioselective synthesis of azabicyclic ring systems: a concise total synthesis of (+)-grandisine D and unnatural analogues

Closing in on azacines: We have developed a new six step approach for the rapid and enantioselective synthesis of indolizidine, pyrrolo[1,2-a]azepine, and pyrrolo[1,2-a]azocine azabicyclic systems and their respective lactam congeners, which are found in a host of natural products as well as pharmaceutical preparations. This protocol enables a concise enantioselective total synthesis of (+)-grandisine?D in 16.4?% overall yield from commercial materials (see scheme).     

First total synthesis of （±）-malaysianone A and （±）-tanariflavanones B

A concise approach for the frst total synthesis of two naturally occurring flavanoids,（）-malaysianone A（1）and（）-tanariflavanones B（2）,has been accomplished with total yields of 12.9%and 10.4%,respectively.The key steps were regioselective deprotection and regioselective synthesis of 5-formaldehyde-8-hydroxy-2-[40-methyl-30-penteneyl]-dihydro-1-benzopyran（8）.     

Asymmetric induction by sulfinyl chirality. A total synthesis of (+)-talaromycin A and (−)-talaromycin B

A total synthesis of (+)-talaromycin A and (−)-talaromycin B was accomplished by means of successive asymmetric induction of all chiral centers using a chiral sulfinyl group.     

A novel and efficient total synthesis of(±)-Cembrene-A

(±)-Cembrene-A,a highly active scent-trail pheromone,was first isolated from thetermite(Nasutitermes exitiosus)and its structure was established by using chemical and spectralmethods,Afterwards,it was also found in some plants and soft corals.In view of itsbiological activity,some total syntheses have been reported.It was reported that its dl-form showed the same order of activity as that of the natural pheromone,In previous work,     

First stereoselective total synthesis of (−)-stagonolide A

The first stereoselective total synthesis of the nonenolide (?)-stagonolide A is described. Olefin metathesis and epoxide opening reaction are the key steps involved.     

First stereoselective total synthesis and reconfirmation of absolute structure of nonenolide (−)-stagonolide D

The first stereoselective total synthesis of nonenolide (?)-stagonolide D has been accomplished. Midland Alpine borane reduction to install hydroxyl group at C4, Henbest epoxidation to introduce epoxide stereoselectively between C7 and C8, Yamaguchi esterification and Olefin metathesis reaction are the key steps involved in the total synthesis.     

Concise total synthesis of (±)-dasyscyphin D

The first and efficient total synthesis of (±)-dasyscyphin D was achieved in 9 steps with 22.6% overall yield. The key steps involved a PtCl(2)-catalyzed pentannulation reaction and acid-catalyzed double Robinson annulations.     

Asymmetric total synthesis of (+)-isocryptotanshinone and formal synthesis of (−)-cryptotanshinone

The first asymmetric total synthesis of (+)-isocryptotanshinone was achieved in 12 linear steps with 12% overall yield from commercially available dihydrobenzopyrone. The key step was a base-mediated cyclization reaction. In addition, the synthetic strategy included the formal synthesis of (−)-cryptotanshinone.     

A stereocontrolled total synthesis of (±)-saframycin A

A thirteen-step total synthesis of (±)-saframycin A from a tricyclic lactam intermediate is described. The key step of this total synthesis is the stereocontrolled construction of a pentacyclic saframycin framework via a modified Pictet-Spengler type cyclization generating a bis-carboxylic acid ester derivative, followed by decarboxylation. The cytotoxicity profiles are also presented.     

A concise total synthesis of (±)-cipadonoid B from synthetic azedaralide

The tetranortriterpene cipadonoid B was efficiently constructed from synthetic azedaralide in a one-pot cascade, via the underutilised ketal-Claisen rearrangement.     

Concise total synthesis of (-)-myxalamide A

The MIDA touch: A concise and highly convergent protecting-group-free total synthesis of (-)-myxalamide?A involves a stereoselective vinylogous Mukaiyama aldol reaction of a vinylketene silyl N,O-acetal, together with a one-pot Stille/Suzuki-Miyaura cross-coupling reaction using Burke's N-methyliminodiacetic acid (MIDA) boronate to connect left- and right-hand fragments of the molecule (see scheme).