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Unified Total Synthesis of Madangamines A, C, and E.

Suto, Takahiro; Yanagita, Yuta; Nagashima, Yoshiyuki; Takikawa, Shinsaku; Kurosu, Yasuhiro; Matsuo, Naoya; Sato, Takaaki; Chida, Noritaka.
J Am Chem Soc; 139(8): 2952-2955, 2017 03 01.
Artigo em Inglês | MEDLINE | ID: mdl-28190360
A stereodivergent strategy for the synthesis of skipped dienes is developed. The method consists of hydroboration of allenes and Migita-Kosugi-Stille coupling, which allows for access to all four possible stereoisomers of the skipped dienes. The hydroboration is especially useful for providing both E-allylic and Z-allylic alcohols from the same allene by simply changing the organoborane reagent. The strategy was successfully applied to a unified total synthesis of the madangamine alkaloids via a common ABCE-tetracyclic intermediate with a (Z,Z)-skipped diene. The late-stage variation of the D-ring enabled the supply of synthetic madangamines A, C, and E for the first time.
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