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Stereoselective Total Synthesis of Dodoneine
Author(s) -
Chinnababu Baggu,
Reddy Sudina Purushotham,
Rao Chitturi Bhujanga,
Rajesh Karuturi,
Venkateswarlu Yenamandra
Publication year - 2010
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/hlca.200900478
Subject(s) - chemistry , stereoselectivity , electrophile , total synthesis , ring closing metathesis , metathesis , pyran , stereochemistry , salt metathesis reaction , combinatorial chemistry , organic chemistry , catalysis , polymer , polymerization
A simple and highly efficient stereoselective total synthesis of dodoneine ( 1 ), a naturally occurring bioactive 5,6‐dihydro‐2 H ‐pyran‐2‐one, was achieved. The synthesis involved Keck 's asymmetric allylation, iodine‐induced electrophilic cyclization, and Grubbs ' catalyzed ring‐closing metathesis as key steps.