Total synthesis and proof of stereochemistry of natural and unnatural pinnaic acids: A remarkable long-range stereochemical effect in the reduction of 17-oxo precursors of the pinnaic acids Journal Article

  

Authors:	Carson, M. W.; Kim, G.; Danishefsky, S. J.
Article Title:	Total synthesis and proof of stereochemistry of natural and unnatural pinnaic acids: A remarkable long-range stereochemical effect in the reduction of 17-oxo precursors of the pinnaic acids
Abstract:	Build 'em up and knock 'em down: natural pinnaic acid and three of its stereoisomers were synthesized from the aldehydes described in the preceding communication. A key step in the synthesis of natural pinnaic acid was a highly stereoselective reduction of ketone 1. The stereochemistry was determined by means of degradation studies of the synthetic material; TBS = tert-butyldimethylsilyl.
Keywords:	unclassified drug; nonhuman; drug structure; drug synthesis; crystal structure; antiinflammatory activity; organic acids; natural product; aldehydes; drug isolation; total synthesis; synthesis (chemical); stereochemistry; ketones; antiinflammatory agent; degradation; natural products; isomers; asymmetric synthesis; sponge (porifera); marine environment; article; phospholipase inhibitor; pinnaic acid; structure elucidation; synthetic materials
Journal Title:	Angewandte Chemie - International Edition
Volume:	40
Issue:	23
ISSN:	1433-7851
Publisher:	Wiley Blackwell
Date Published:	2001-12-03
Start Page:	4453
End Page:	4456
Language:	English
DOI:	10.1002/1521-3773(20011203)40:23<4453::aid-anie4453>3.0.co;2-4
PROVIDER:	scopus
PUBMED:	12404443
DOI/URL:	http://www.scopus.com/inward/record.url?eid=2-s2.0-0035803649&partnerID=40&md5=ceb6a0bc5417e91b747ada3abb8eaa8c
Notes:	Export Date: 21 May 2015 -- Source: Scopus

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