Stereoselective Synthesis of Steroids and Related Compounds, V. Synthesis of (±)‐Chokol A by a Tandem Michael‐Addition/Dieckmann Cyclization | Zendy

Groth Ulrich | Zendy; Halfbrodt Wolfgang | Zendy; Köhler Thomas | Zendy; Kreye Paul | Zendy

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Stereoselective Synthesis of Steroids and Related Compounds, V. Synthesis of (±)‐Chokol A by a Tandem Michael‐Addition/Dieckmann Cyclization

Author(s) -

Groth Ulrich,

Halfbrodt Wolfgang,

Köhler Thomas,

Kreye Paul

Publication year - 1994

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.199419940907

Subject(s) - chemistry , tandem , stereoselectivity , conjugate , bromide , yield (engineering) , michael reaction , total synthesis , stereochemistry , organic chemistry , catalysis , mathematical analysis , materials science , mathematics , metallurgy , composite material

A total synthesis of (±)‐chokol A ( rac ‐ 12 ) was accomplished in five steps by starting from the α,β‐unsaturated ester ( E )‐ 2 in an overall yield of 24%. The key step of this synthesis is the tandem conjugate addition/Dieckmann cyclization of the cuprate derived from vinyl bromide 9 with the α,β‐unsaturated ester ( E )‐ 2 .

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