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An Approach Toward the Bridged 14‐Membered Carbon Macrocycle of Bielschowskysin
Author(s) -
Farcet JeanBaptiste,
Mulzer Johann,
Himmelbauer Martin K.
Publication year - 2016
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.201600271
Subject(s) - chemistry , tetradecane , intramolecular force , diterpene , carbonylation , alkylation , lactone , halide , palladium , sequence (biology) , stereochemistry , catalysis , organic chemistry , biochemistry , carbon monoxide
Relying on our previous achievements toward the a total synthesis of bielschowskysin,[1][J.‐B. Farcet, 2012], [2][J.‐B. Farcet, 2013], [3][M. Himmelbauer, 2013], [4][M. Himmelbauer, 2013], [5][J.‐B. Farcet, 2013] we herein report additional efforts to close the bridged tetradecane carbocyclic core of this marine diterpene. The key step of this strategy is an intramolecular alkylation between a cis ‐substituted vinyl halide and a lactone that were accessed by a diastereoselective propargylation/hydrogenation sequence and palladium‐catalyzed carbonylation, respectively.