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Progress towards the total synthesis of guanacastepene A. Approaches to the construction of quaternary carbons and the 5-7-6 tricyclic carbon skeleton

✍ Scribed by Truc M. Nguyen; Daesung Lee

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 74 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00729-3

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✦ Synopsis

The construction of the 5-7-6 tricyclic skeleton of guanacastepene A, including the quaternary carbons, has been achieved. The C-11 and C-8 quaternary carbons were constructed by cuprate addition and carbene insertion, respectively. The 5-7-6 tricyclic core was generated by a selective aldol and SmI 2 -induced intramolecular aldehyde-alkene coupling.

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