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This content will become publicly available on March 14, 2026

Title: Studies Toward the Synthesis of Leiodolide A
ABSTRACT: Studies have described a highly convergent plan toward the synthesis of leiodolide A (1), a potent cytotoxic sponge metabolite. The enantiocontrolled preparation of aldehyde 6 is achieved with the application of several advances of methodology for the synthesis of substituted 1,3-oxazoles. Efforts have examined the halogen dance reaction, the selectivity of Stille cross coupling reactions of 4-bromo-1,3-oxazoles, and nucleophilic displacement of the 2-phenylsulfonyl substitu-ent with organolithium reagents as preparatively useful reactions. These techniques have facilitated the efficient synthesis of 6 from the starting bromide 12, alkenylstannane 16 and the primary nonracemic alcohol 25.  more » « less
Award ID(s):
2102587
PAR ID:
10637328
Author(s) / Creator(s):
; ;
Publisher / Repository:
American Chemical Society
Date Published:
Journal Name:
Organic Letters
Volume:
27
Issue:
10
ISSN:
1523-7060
Page Range / eLocation ID:
2279 to 2283
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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