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A carbonylative cross-coupling strategy to the total synthesis of the sarcodictyins: preliminary studies and synthesis of a cyclization precursor

✍ Scribed by Simona M Ceccarelli; Umberto Piarulli; Joachim Telser; Cesare Gennari

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
81 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Preliminary studies were conducted on the implementation of a new strategy to the total synthesis of the common diterpenoid tricyclic skeleton of sarcodictyins and eleutherobin. According to the approach presented, a key retrosynthetic disconnection is devised at the C3-C5 position, identifying a carbonylative cross-coupling reaction as the medium-sized ring forming step. The synthesis of a fully functionalized cyclization precursor, comprising a Z vinylstannane and a carboalkoxy-substituted Z enol triflate as reactive centres, is described.

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