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Norrisolide: Total Synthesis and Related Studies
Author(s) -
Brady Thomas P.,
Kim Sun Hee,
Wen Ke,
Kim Charles,
Theodorakis Emmanuel A.
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500513
Subject(s) - lactol , bicyclic molecule , lactone , stereochemistry , ring (chemistry) , natural product , baeyer–villiger oxidation , chemistry , total synthesis , steric effects , stereoselectivity , combinatorial chemistry , organic chemistry , catalysis
A stereoselective synthesis of (+)‐norrisolide is presented. This natural product belongs to a family of marine spongiane diterpenes the structure of which is characterized by a fused γ‐lactone–γ‐lactol ring system attached to a bicyclic hydrophobic core. Our studies led to the development of a expedient synthesis of such γ‐lactone–γ‐lactol motifs based on ring expansion of a fused cyclopropyl ester. Highlights of the synthetic strategy toward norrisolide include the coupling of the two bicyclic systems by constructing a sterically demanding C9C10 bond and the installation of the C19 oxygen at the last step of the synthesis via a Baeyer–Villiger oxidation.