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Enantioselective Total Synthesis of (–)‐Subglutinols A and B: Potential Immunosuppressive Agents Isolated from a Microorganism
Author(s) -
Kikuchi Takuya,
Mineta Mayuko,
Ohtaka Jingo,
Matsumoto Naoko,
Katoh Tadashi
Publication year - 2011
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.201100517
Subject(s) - chemistry , moiety , enantioselective synthesis , stereochemistry , decalin , total synthesis , ring (chemistry) , pyrone , tetrahydrofuran , derivative (finance) , ether , organic chemistry , catalysis , solvent , financial economics , economics
Potential immunosuppressive diterpenoid pyrones (–)‐subglutinols A and B were efficiently synthesized in an enantioselective manner starting from a known trans ‐decalone derivative. The synthetic method involved the following key steps: (i) [2,3]‐Wittig rearrangement of a stannyl methyl ether to access the requisite decalin segment; (ii) coupling of the decalin segment with a γ‐pyrone moiety to set up the desired carbon framework; (iii) construction of a characteristic tetrahydrofuran ring in one‐pot fashion through an internal S N 2‐type cyclization, and (iv) conversion of a γ‐pyrone moiety into an α‐pyrone ring to yield the target (–)‐subglutinols A and B.