The preparation of 9-substituted Δ5-octenolides: Synthesis of 8-deoxy-pseudo-ascidiatrienolide C

Tetrahedron

Volumn 52, Issue 6, 1996, Pages 2113-2124

  McNaughton Smith, Grant A ^a   Taylor, Richard J K ^a,b  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0030034367     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01028-9     Document Type: Article

References (42)

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33. Attempted conversion of alkyne (15b), as its methyl ester, into (14c) via hydrostannylation using either heat or UV light resulted in partial isomerisation of the 4,5-double bond, although the vinylstannane was formed exclusively as the E-isomer.
34. The Corey-Nicolaou and Yamaguchi procedures were also tried with substrates (15a-c) but lactonisation was not observed [diolide fomation was seen, however, occurring in 60% yield with (15a) under Corey-Nicolaou conditions].
35. 5 was unchanged during hydrostannylation (see note 18) as cis-alkenes are thermodynamically preferred in 9 membered rings: Cope, A. C.; Moore, P. T; Moore, W. R. J. Am. Chem. Soc., 1959, 81, 3153.
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