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Total synthesis and assignment of configuration of lissoclinamide 7

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Wipf, P and Fritch, PC (1996) Total synthesis and assignment of configuration of lissoclinamide 7. Journal of the American Chemical Society, 118 (49). 12358 - 12367. ISSN 0002-7863

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Abstract

The first total synthesis of lissoclinamide 7, a 21-membered cyclopeptide isolated from Lissoclinum bistratum, was accomplished in 23 steps and 4.4% overall yield. The extraordinary configurational lability of the thiazoline segments was overcome by a novel strategy combining the use of the Burgess reagent for multiple simultaneous oxazoline and thiazoline formations and an efficient oxazoline → thiazoline heterocycle interconversion. In addition to the total synthesis, this work highlights the scope of alternative strategies toward Lissoclinum peptides and presents the preparation of analogues for SAR studies of the cytotoxic effects of this family of marine natural products.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Fritch, PC
Date: 1 December 1996
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 118
Number: 49
Page Range: 12358 - 12367
DOI or Unique Handle: 10.1021/ja962859f
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
Date Deposited: 22 Jul 2015 13:14
Last Modified: 30 Oct 2017 23:57
URI: http://d-scholarship.pitt.edu/id/eprint/25643

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