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Total Synthesis and Assignment of Configuration of Lissoclinamide 7

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journal contribution
posted on 11.12.1996, 00:00 by Peter Wipf, Paul C. Fritch
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.