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Volumn 7, Issue 4, 2005, Pages 545-548

The stille reaction in the synthesis of carotenoid butenolides: Synthesis of S′-epi-pridinin

Author keywords

[No Author keywords available]

Indexed keywords

6' EPIPERIDININ; ALKANE DERIVATIVE; ALKENYL GROUP; BUTENOLIDE; CAROTENOID; HALIDE; UNCLASSIFIED DRUG;

EID: 14844345109     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0478281     Document Type: Article
Times cited : (63)

References (57)
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    • note
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    • The stereochemical outcome (Z > E) of the modified-Julia reaction involving BT-allyl sulfones is general in the construction of polyenes, as we confirmed in other model systems as well as in the construction of the entire peridinin skeleton using this reaction as last step. We revisited our assignment of the geometry of a pentaenylbis-stannane (ref 4) and found it to be in error (should be corrected to Z) (Vaz, B.; Álvarez, R.; Souto, J. A.; de Lera, A. R. Synlett 2005, in press). Since the final carotenoids have all-E geometry, we surmised that isomerization had taken place in the final double Stille reaction by the action of palladium catalyst, most likely acting on the carotenoid skeleton.
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