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Highly convergent total synthesis and assignment of absolute configuration of majusculamide D, a potent and selective cytotoxic metabolite from Moorea sp

TitleHighly convergent total synthesis and assignment of absolute configuration of majusculamide D, a potent and selective cytotoxic metabolite from Moorea sp
Publication TypeJournal Article
Year of Publication2019
AuthorsCaro-Diaz E.JE, Valeriote F.A, Gerwick WH
JournalOrganic Letters
Volume21
Pagination793-796
Date Published2019/02
Type of ArticleArticle
ISBN Number1523-7060
Accession NumberWOS:000457947900047
Keywordsalkenes; catalyzed asymmetric carboalumination; chemistry; efficient; microcolin-b; natural-products
Abstract

The total synthesis of majusculamide D (MJS-D) is described, a lipopentapeptide originally isolated from Lyngbya majuscula and reisolated from a Moorea sp. MJS-D possesses selective and potent cancer cell toxicity. A scalable and convergent strategy with a minimal number of purifications produced significant quantities of MJM-D for in vivo evaluations. The absolute configuration of the 1,3-dimethyl-octanamide motif was determined by synthesis of this fragment via ZACA chemistry.

DOI10.1021/acs.orglett.8b04050
Short TitleOrg. Lett.
Student Publication: 
No
Research Topics: