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Catalytic Enantioselective Synthesis of ( S )‐8‐Hydroxy‐3‐[( S )‐2′‐hydroxypentyl]‐6‐methoxyisochroman‐1‐one, ( S )‐3‐Hydroxy‐3‐[( S )‐2′‐hydroxypentyl]‐6,8‐dimethoxyisochroman‐1‐one, and Their Epimers
Author(s) -
Kumaraswamy Gullapalli,
Ankamma Kukkadapu,
Raghu Nimmakayala,
RamBabu Dasa
Publication year - 2014
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.201301708
Subject(s) - enantioselective synthesis , chemistry , catalysis , epimer , stereochemistry , chirality (physics) , organic chemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
The total synthesis of ( S )‐8‐hydroxy‐3‐[( S )‐2′‐hydroxypentyl]‐6‐methoxyisochroman‐1‐one, ( S )‐3‐hydroxy‐3‐[( S )‐2′‐hydroxypentyl]‐6,8‐dimethoxyisochroman‐1‐one, and their epimers has been successfully achieved. The key reactions include a catalytic enantioselective asymmetric epoxidation to introduce the chirality, and an Alder–Rickert reaction for the construction of the substituted phenyl ring.