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First Total Synthesis of (±)‐Celaphanol A
Author(s) -
Bie Pingyan,
Zhang Chenglu,
Li Anpai,
Peng Xuanjia,
Wu Tongxing,
Pan Xinfu
Publication year - 2002
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200200089
Subject(s) - chemistry , intramolecular force , tricyclic , total synthesis , stereochemistry , keto–enol tautomerism , chloride , medicinal chemistry , organic chemistry , tautomer
The first total synthesis of (±)‐Celaphanol A was accomplished starting from α‐cyclocitral and 3,4‐dimethoxy benzyl chloride in six steps. The intramolecular cyclization with BF 3 ·Et 2 O and enolization in t ‐BuOK/ t ‐BuOH were the key steps. The process of intramolecular cyclization afforded an all‐ cis isomer intermediate for synthesis of aromatic tricyclic diterpenes.