Premium
Enantioselective Total Synthesis and Absolute Configuration of the Natural Norsesquiterpene 7‐Demethyl‐2‐methoxycalamenene by a Silane‐Terminated Intramolecular Heck Reaction
Author(s) -
Tietze Lutz F.,
Raschke Thomas
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619961207
Subject(s) - chemistry , enantioselective synthesis , heck reaction , absolute configuration , intramolecular force , total synthesis , yield (engineering) , silane , stereochemistry , organic chemistry , medicinal chemistry , catalysis , palladium , materials science , metallurgy
The total synthesis of the norsesquiterpene 7‐demethyl‐2‐methoxycalamenene ( 1 ) by a newly developed enantioselective silane‐terminated Heck reaction is described. The Pd 0 ‐catalyzed transformation of the allylsilane 7 , obtained from 3‐(3‐methoxyphenyl)propanol ( 2 ) in 7 steps, provides the tetralin 8 in 91% yield and with 92% ee in the presence of ( R )‐BINAP. Transformation of 8 via 14 and 15 gives 1 . The absolute configuration of 1 which has previously not been known was deduced from a single‐crystal X‐ray analysis of 10 , obtained from the cyclization product 8 by hydroboration and acylation with camphanic acid chloride.