Approaches to the Synthesis of Cytochalasans. Part 11 . Further transformations and cyclization attempts directed towards proxiphomin | Zendy

Boutellier Markus | Zendy; Wallach Daniel | Zendy; Tamm Christoph | Zendy

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Approaches to the Synthesis of Cytochalasans. Part 11 . Further transformations and cyclization attempts directed towards proxiphomin

Author(s) -

Boutellier Markus,

Wallach Daniel,

Tamm Christoph

Publication year - 1993

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.19930760710

Subject(s) - chemistry , umpolung , steric effects , phosphonate , reactivity (psychology) , condensation , scheme (mathematics) , condensation reaction , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry , catalysis , medicine , mathematical analysis , physics , alternative medicine , mathematics , pathology , nucleophile , thermodynamics

Starting from iodoalcohol 9 , the monoprotected dialdehyde 5 was synthesized ( Scheme 2 ) and converted to 17 by reaction with oxo‐phosphonate 15 ( Scheme 3 ). The latter was prepared from 13 . Cyclisation of 17 to the target compound 18 failed. Also the attachment of thiol 22 to lactone 19 was unsatisfactory ( Scheme 4 ). Therefore, the building blocks 28 and 29 were synthesized using diene 33 and diester 30 as starting material for 28 and 9 for 29 ( Scheme 5 and 6 ). Hydroxy acid 28 was converted into formyl‐ester 46 ( Scheme 7 ). However, the condensation of its derivatives 48 and 49 with ‘Umpolung’ of the carbonyl reactivity was unsuccessful, probably due to steric hindrance.

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