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Formal Total Synthesis of (+)‐Dihydromevinolin via a Chelate‐Controlled Intramolecular Diels‐Alder Reaction as the Key Step
Author(s) -
Schnaubelt Jürgen,
Frey Barbara,
Reissig HansUlrich
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19990505)82:5<666::aid-hlca666>3.0.co;2-8
Subject(s) - chemistry , intramolecular force , diels–alder reaction , total synthesis , natural product , enone , chelation , formal synthesis , carboxylate , stereochemistry , stereoselectivity , organic chemistry , catalysis
Compound 3 was synthesized efficiently from enone 4 via (silyloxy)cyclopropanecarboxylate intermediates 6 and 7 . A chelate‐controlled intramolecular Diels‐Alder reaction of 3 afforded the octahydronaphthalene‐2‐carboxylate isomer trans ‐ 2b as the main product. This compound was stereoselectively converted into the known dihydromevinolin precursor 1 , thus providing a formal total synthesis of this natural product.