The synthesis of a combretastatin A-4 based library and discovery of new cooperative ortho-effects in Wittig reactions leading to (Z)-stilbenes

Synlett

Volumn , Issue 18, 2006, Pages 2977-2980

  Harrowven, David C ^a   Guy, Ian L ^a   Howell, Melanie ^b   Packham, Graham ^b  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Alkenes; Antitumor agents; Stereoselective synthesis; Total synthesis; Wittig reactions

Indexed keywords

(2 BROMO 3,4,5 TRIMETHOXYBENZYL)TRIPHENYLPHOSPHONIUM BROMIDE; 1 [2 (3 HYDROXY 2 IODO 4 METHOXYPHENYL) 1 ETHENYL] 2 BROMO 3,4,5 TRIMETHOXYBENZENE; 1 [2(3 ALLYLOXY 2 IODO 4 METHOXYPHENYL) 1 ETHYL] 2 BROMO 3,4,5 TRIMETHOXYBENZENE; ANTINEOPLASTIC AGENT; COMBRETASTATIN A4; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG EFFECT; DRUG SYNTHESIS; STEREOCHEMISTRY; WITTIG REACTION;

EID: 33751283824     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-948200     Document Type: Article

References (19)

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15. Conversely, o-methoxybenzaldehydes generally promote formation of (Z)-stilbenes. See: (b) Yamataka, H.; Nagareda, K.; Ando, K.; Hanafusa, T. J. Org. Chem. 1992, 52, 2865.
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18. Supplementary information providing characterization data for each of the (Z)-stilbenes reported herein, together with details of their preparation and the method of purification: employed, is available from the author.
19. 1 116 °C). Following recrystallization of our synthetic sample from either EtOAc or EtOAc-hexane, it gave mp 83-84 °C (recorded in duplicate on two separate apparatuses).