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Regio‐ and Stereoselective Functionalizations of Tricyclo [3.3.0.0 2,8 ]octan‐3‐one, a Potential Synthon for Polycyclopentanoid Terpenes and Prostacyclin Analogs. Preliminary Communication
Author(s) -
Demuth Martin,
Chandrasekhar Sosale,
Nakano Koichi,
Raghavan Palaykotai R.,
Schaffner Kurt
Publication year - 1980
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.19800630837
Subject(s) - synthon , chemistry , stereoselectivity , terpene , annulation , prostacyclin , stereochemistry , ring (chemistry) , organic chemistry , catalysis , biochemistry
Chemical transformation of tricyclo [3.3.0.0 2,8 ]octan‐3‐one (1) have been carried out in order to explore its potential utility as a versatile synthon for polycyclopentanoid terpenes and prostacyclin analogs. Various functionalizations of rings A and B and annulation of a third ring C were achieved in generally high yields. The system provides for a large measure of regio‐ and stereoselective reaction control.