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Studies towards the total synthesis of hygrocins A and B |
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| Authors: | Sivappa Rasapalli Gopalakrishna Jarugumilli Gangadhara Rao Yarrapothu Hamza Ijaz James A Golen Paul G Williard |
| Institution: | 1. Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, MA 02747, United States;2. Department of Chemistry, Brown University, Providence, RI 02912, United States |
| Abstract: | The western segment of hygrocins A–B has been synthesized through the coupling of a chiral C5–C13 synthon with the sterically demanding hexasubstituted naphthalenic core. The C5–C13 chiral fragment has been assembled via a stereoselective Johnson orthoester rearrangement of an optically pure allylic alcohol derived from d-glucose. Our studies lay the platform for the determination of the absolute configuration of the unassigned C8-stereocenter of the title compounds in addition to the completion of the total synthesis of the unique ansamacrolides hygrocins A and B. |
| Keywords: | Ansamycins Divergolides Claisen rearrangement Naphthoquinone Non-biomimetic |
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