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Total Synthesis of a 6,6‐Spiroketal Metabolite, Dinemasone A
Author(s) -
Raji Reddy Chada,
Srikanth Boinapally,
Dilipkumar Uredi,
Rao Kakita Veera Mohana,
Jagadeesh Bharatam
Publication year - 2013
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.201201246
Subject(s) - chemistry , total synthesis , stereoselectivity , metabolite , intramolecular force , stereochemistry , sharpless epoxidation , alcohol , enantioselective synthesis , diol , acetal , organic chemistry , catalysis , biochemistry
The stereoselective total synthesis of dinemasone A has been accomplished. The key reactions, Sharpless asymmetric epoxidation, lithium‐mediated epoxy alcohol opening, and double‐intramolecular hetero‐Michael addition, gave access to dinemasone A from lactic acid esters. The stereochemistry at the spiro carbon was determined using extensive NMR studies.