Approaches to the synthesis of cytochalasans. Part 7 . Synthesis of some building blocks for the construction of the macrocyclic moiety | Zendy

Wallach Daniel | Zendy; Csendes Ivan G. | Zendy; Burckhardt Peter E. | Zendy; Schmidlin Tibur | Zendy; Tamm Christoph | Zendy

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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.

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