A Convenient Synthesis of (4 R ,7 Z ,11 Z )‐(‐)‐4‐Methylheptadeca‐7,11‐dienal and (4 R ,7 Z ,11 Z )‐4‐Methylheptadeca‐7,11‐dienoic Acid | Zendy

Sharma Anubha | Zendy; Chattopadhyay Subrata | Zendy

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A Convenient Synthesis of (4 R ,7 Z ,11 Z )‐(‐)‐4‐Methylheptadeca‐7,11‐dienal and (4 R ,7 Z ,11 Z )‐4‐Methylheptadeca‐7,11‐dienoic Acid

Author(s) -

Sharma Anubha,

Chattopadhyay Subrata

Publication year - 1996

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199619960411

Subject(s) - chemistry , regioselectivity , bromide , epoxide , alkylation , wittig reaction , aldehyde , enantiomer , derivative (finance) , medicinal chemistry , antifungal , stereochemistry , organic chemistry , catalysis , medicine , dermatology , financial economics , economics

A synthesis of the title aldehyde 1 and acid 2 , the ( R ) enantiomers of the antifungal and antibacterial principles of Sporothrix species, was developed. Alkylation of the alkynol derivative 6 with ( S )‐citronellyl bromide ( 5 ), depyranylation, cis hydrogenation, PCC oxidation, and Z‐selective Wittig reaction with hexylidenephosphorane gave the hydrocarbon 11 . Its regioselective epoxidation and cleavage of the epoxide with HlO 4 affords ( R )‐ 1 which was oxidized to ( R )‐ 2 .

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