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Synthesis of (±)‐Sterpurene and Hydroxylated Derivatives by 1,6‐Addition of Organocuprates to Acceptor‐substituted Enynes
Author(s) -
Krause Norbert
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930186
Subject(s) - chemistry , regioselectivity , intramolecular force , trifluoromethanesulfonate , lithium (medication) , acceptor , tricyclic , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , medicine , physics , condensed matter physics , endocrinology
The synthesis of (±)‐sterpurene ( 1 ), 14‐/15‐hydroxysterpurene ( 13 ), and 11,14‐/11,15‐dihydroxysterpurene ( 14 ) is described. Key steps are the 1,6‐addition of lithium dimethylcuprate to the 2‐en‐4‐ynoate 11 and the regioselective trapping of the allenyl enolate with methyl triflate. The vinylallene 6 thus obtained undergoes an intramolecular Diels‐Alder reaction to give the tricyclic ester 5 , which serves as a common precursor of 1 , 13 , and 14 .