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The First Total Synthesis of (±)-Terpestacin, HIV Syncytium Formation Inhibitor

✍ Scribed by Kuniaki Tatsuta; Naoyuki Masuda; Hidemitsu Nishida

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
600 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

Terpcstacin has beensynthesizedthroughC-alkylation of ~-ketolactone9 widrchain portion12.'rlresctwocompounds werederivedfrom2-cyclopcrrten-l-ylactic acid andE,E-farnesol, tI?sptXtively. 01997 ElsevierScience Ltd. AU rights reserved.

Terpestacin( ) is a bicyclo5-15-fusedsesterterpeneisolatedfromArthriniumsp. metabolizesas a novel syncytium formation inhibitor in HIV infection.1)The absolutestructurehas been determined by chemical studies and X-ray crystallography.2)Independently,the same compoundhas been reported as a phytotoxin from Bipolaris cynodontis.s) The acetate 2 (proliferin)was also isolated as a mycotoxin from Fusarium prol~eratum.a)Previoussyntheticapproachesto tetpestacin(1) are few, althoughan elegant model studyhas beenreportedby Yoshii'sgroup.5)We describeherethe first total synthesisof (+erpestacin (1) whichsolves theproblemof establishingthe properrelativecontlgumtions.

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