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A Biomimetic Synthesis of Sacculatane Diterpenoids
Author(s) -
Grinco Marina,
Kulciţki Veaceslav,
Ungur Nicon,
Vlad Pavel F.,
Gavagnin Margherita,
Castelluccio Francesco,
Cimino Guido
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890031
Subject(s) - chemistry , biomimetic synthesis , stereochemistry , combinatorial chemistry , diterpene
The biomimetic synthesis of sacculatane‐type epimeric compounds 14a and 14b is reported. The key synthetic step is the low‐temperature superacidic cyclization of (all‐ E )‐ ω ‐acetoxygeranylgeraniol 12 obtained in nine steps from geranyllinalool ( 13 ). The 19‐acetoxysacculata‐7,17‐dien‐11‐ol ( 14a ) could be an important and convenient starting compound for the synthesis of other sacculatane diterpenoids.