Stereoselective total synthesis of (+)-cardiobutanolide

Stereoselective synthesis of styryllactone (+)-cardiobutanolide was accomplished in good overall yield from d-(-)-tartaric acid. Key features of the synthesis include the elaboration of a gamma-hydroxy butyramide obtained from the dimethylamide of tartaric acid, involving a combination of the addition of 1,3-dithian-2-yllithium and stereoselective reduction.     

Stereoselective total synthesis of (+)-aspicilin

A stereoselective synthesis of (+)-aspicilin is described. Regio- and stereoselective functionalization by intramolecular participation of the sulfinyl group, ene reaction, and macrolactonization by Wadsworth-Emmons reaction employing Masamune-Roush protocol are the key steps of the route.     

Stereoselective total synthesis of (+)-boronolide

A seteroselective total synthesis of (+)-boronolide is described. The key steps are Sharpless asymmetric dihydroxylation, Shibasaki's asymmetric Henry reaction, asymmetric allylation and ring closing metathesis.     

Stereoselective total synthesis of (+)-varitriol

Stereoselective total synthesis of (+)-varitriol, an antitumor natural product, was accomplished by two versatile strategies starting from the commercially available d-(−)-ribose and ethyl (S)-lactate. The key steps involved in the synthesis of the target molecule are epoxidation, cyclization, dihydroxylation and Diels-Alder reaction.     

Stereoselective total synthesis of (+)-artemisinin

The total synthesis of the novel antimalarial drug, a sesquiterpene endoperoxide, (+)-artemisinin is described. The approach is flexible and stereoselective. The use of an intermolecular radical reaction on an intermediate iodolactone and a Wittig reaction on a ketone were employed for the synthesis.     

Stereoselective total synthesis of (+)-sapinofuranone B

Two approaches for the total synthesis of (+)-sapinofuranone B have been described. The first strategy utilizes the methodology developed earlier in our group to get the chiral propargyl alcohol and the second strategy involves generation of threo-1,2-diol derivative by diastereoselective and enantioselective addition of [(Z)-γ-methoxymethoxyallyl]diisopinocampheylborane onto aldehyde and cross metathesis as the key steps.     

Stereoselective total synthesis of (+)-synargentolide A

The stereoselective synthesis of synargentolide A, a polyhydroxy δ-lactone, has been accomplished from tartaric acid. The key steps in the synthesis involve Keck and Brown allylations and ring closing metathesis.     

Stereoselective total synthesis of (+)-polyrhacitide A

A facile stereoselective total synthesis of secondary metabolite (+)-polyrhacitide A is described. Stereoselective aldol reaction, Horner-Wardsworth-Emmons reaction, Evans acetal intramolecular oxa-Michael reaction and diastereoselective syn reduction reaction are the key steps involved in the target synthesis.     

Stereoselective total synthesis of (+)-myriocin from D-mannose

The stereoselective total synthesis of myriocin 1 from D-mannose is described; the carbon framework with three contiguous chiral centers including a tetra-substituted carbon with nitrogen was effectively constructed using Overman rearrangement as the key reaction.     

Synthetic studies on (+)-aplasmomycin. 2. Stereoselective synthesis of Corey''s key intermediate, a formal total synthesis

The C-3 C-11 segment of (+)-aplasmomycin was synthesized stereoselectively starting from (+)-pantolactone ( ) and the C-3 C-17 segment was synthesized via coupling of and .     

Stereoselective total synthesis of antitumor macrolide (+)-rhizoxin D

[structure: see text] A convergent, stereoselective total synthesis of the macrolide antitumor agent rhizoxin D is described. (+)-DIPCl-promoted asymmetric aldol reaction, Evans-Tishchenko 1,3-diol synthesis, modified Julia coupling, and Horner-Wadsworth-Emmons reactions are featured.     

Stereoselective total synthesis of (+)-anamarine via cross-metathesis protocol

A convergent stereoselective total synthesis of (+)-anamarine via cross-metathesis (CM) protocol starting from 2-butyn-1,4-diol and vinyl lactone is reported. Other key features of the strategy include the use of Sharpless asymmetric epoxidation, Sharpless dihydroxylation, and Red-Al reduction.     

Enantiospecific formal total synthesis of (+)-dihydrokawain-5-ol

Abstract

Formal total synthesis of dihydrokawain-5-ol is accomplished starting from tartaric acid. Key reactions include Horner–Wadsworth–Emmons olefination, sodium borohydride mediated stereoselective reduction, orthogonal protection and deprotection of alcohols and ring closing metathesis.     

Catalytic asymmetric formal total synthesis of (+)-dichroanone and (+)-taiwaniaquinone H

Catalytic asymmetric formal total synthesis of (+)-dichroanone and (+)-taiwaniaquinone H has been achieved. Key step involved construction of all-carbon quaternary carbon by palladium-catalyzed conjugate addition of arylboronic acid to 3-methyl cyclohexenone. Furthermore, a new approach to build [6-5-6] tricyclic backbone via formyl introduction and subsequent aldol-type condensation was also explored.     

Stereoselective synthesis of (+)-diplodialides-B,C and a formal synthesis of (+)-diplodialide-A by ring-closing metathesis approach

Stereoselective synthesis of diplodialides-B and C and the formal synthesis of diplodialide-A are reported. A combination of Jacobsen’s hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centers, while a ring-closing metathesis strategy was used for the construction of the lactone ring.     

Stereoselective formal synthesis of (+)-allokainic acid via thiol-mediated acyl radical cyclization

Stereoselective formal synthesis of (+)-allokainic acid was accomplished starting from L-glutamate by using a thiol-mediated acyl radical cyclization as a key step. The cyclization of a formylalkenoate proceeded in a highly diastereoselective manner to give trans-4,5-disubstituted pyrrolidin-3-one without the production of the cis-isomer. The pyrrolidinone was then converted into the established synthetic intermediate of (+)-allokainic acid via the iron-catalyzed coupling reaction with an isopropenyl Grignard reagent.     

Asymmetric total synthesis and formal total synthesis of the antitumor sesquiterpenoid (+)-eremantholide A

[structure: see text]. A new asymmetric total synthesis of (+)-eremantholide A is reported in which a Hoveyda-Grubbs ring-closing metathesis (RCM) reaction is used to assemble the nine-membered oxonin ring, and an enolate alkylation between the 3(2H)-furanone 2 and O-triflate 3 is exploited for C(9)-C(10) bond construction. An Evans asymmetric aldol reaction and a Sharpless asymmetric epoxidation served to stereoselectively install the C(6), C(7), and C(8) stereocenters of the target structure.