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An Economical and Practical Synthesis of rac ‐( Z )‐β‐Santalol: Application of a Scriabine‐Inspired Reaction to Alkenes Results in the One‐Step Preparation of a Key Intermediate
Author(s) -
Birkbeck Anthony A.,
Marquet Xavier,
Millet Pascal,
Pamingle Hervé
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403219
Subject(s) - chemistry , alkene , yield (engineering) , total synthesis , cyclopentadiene , combinatorial chemistry , sequence (biology) , substrate (aquarium) , stereochemistry , organic chemistry , catalysis , materials science , biochemistry , oceanography , metallurgy , geology
An economical and practical synthesis of rac ‐( Z )‐β‐santalol was accomplished. The key coupling step is based on a Scriabine‐inspired reaction of a dienyl diacetate substrate and an alkene. The total synthesis was achieved in five steps (longest linear sequence) in 19 % overall yield from cyclopentadiene.