Convergent Total Synthesis of (-)-Cyclopamine.

Autor:	Sofiadis M; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States., Xu D; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States., Rodriguez AJ; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States., Nissl B; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States., Clementson S; Research and Early Development, LEO Pharma A/S, 2750 Ballerup, Denmark., Petersen NN; Research and Early Development, LEO Pharma A/S, 2750 Ballerup, Denmark., Baran PS; Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2023 Oct 11; Vol. 145 (40), pp. 21760-21765. Date of Electronic Publication: 2023 Oct 02.
DOI:	10.1021/jacs.3c09085
Abstrakt:	A concise and enantioselective total synthesis of the Veratrum alkaloid cyclopamine is disclosed. This highly convergent synthesis with a 16-step longest linear sequence (LLS) was enabled by a de novo synthesis of the trans -6,5-heterobicycle via a strain-inducing halocyclization process, a key Tsuji-Trost cyclization to construct the fully substituted, spirocyclic THF motif with exquisite diastereocontrol, and a late-stage ring-closing metathesis (RCM) reaction to forge the central tetrasubstituted olefin.
Databáze:	MEDLINE
Externí odkaz:	Zobrazit plný text záznamu