Stereoselective Total Synthesis of (+)‐Nephrosteranic Acid and (+)‐Roccellaric Acid through Asymmetric Dihydroxylation and Johnson–Claisen Rearrangement | Zendy

Fernandes Rodney A. | Zendy; Chowdhury Asim K. | Zendy

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Stereoselective Total Synthesis of (+)‐Nephrosteranic Acid and (+)‐Roccellaric Acid through Asymmetric Dihydroxylation and Johnson–Claisen Rearrangement

Author(s) -

Fernandes Rodney A.,

Chowdhury Asim K.

Publication year - 2011

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.201001419

Subject(s) - dihydroxylation , chemistry , claisen rearrangement , stereoselectivity , regioselectivity , yield (engineering) , total synthesis , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , materials science , metallurgy

An efficient stereoselective total synthesis of (+)‐nephrosteranic acid and (+)‐roccellaric acid is presented. The synthetic strategy features the regioselective asymmetric dihydroxylation of the γ,δ‐olefinic bond of a α,β,γ,δ‐unsaturated ester and the Johnson–Claisen rearrangement as the key steps. The synthesis is achieved in 10 steps and 6.8 % (nephrosteranic acid) and 7.6 % (roccellaric acid) overall yield.

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