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Approaches to the synthesis of cytochalasans. Part 7 . Synthesis of some building blocks for the construction of the macrocyclic moiety
Author(s) -
Wallach Daniel,
Csendes Ivan G.,
Burckhardt Peter E.,
Schmidlin Tibur,
Tamm Christoph
Publication year - 1984
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.19840670737
Subject(s) - chemistry , synthon , moiety , tetrahydropyran , phosphonium , bromide , pulegone , stereochemistry , phosphonium salt , organic chemistry , ring (chemistry) , salt (chemistry) , chromatography , essential oil
The synthesis of ethyl (2 E , 4 E , 8 R )‐8‐methyl‐10‐[(2 H ‐tetrahydropyran‐2‐yl)oxy]‐2,4‐decadienoate ( 11 ), methyl (2 E , 8 R )‐8‐methyl‐10‐[(2 H ‐tetrahydropyran‐2‐yl)oxy]‐2‐decenoate ( 16 ), synthons for the construction of the macrocyclic moieties of the cytochalasins A, B and F, and of (3 R )‐[7‐(1,3‐dioxolan‐2‐yl)‐3‐methylheptyl]triphenyl‐phosphonium bromide ( 24 ), a C 8 ‐building block for deoxaphomin, proxiphomin and protophomin is described. In all instances (+)‐( R )‐pulegone ( 5 ) served as starting material.