Polyketide assembly by alkene-alkyne reductive cross-coupling: Spiroketals through the union of homoallylic alcohols

Journal of the American Chemical Society

Volumn 132, Issue 22, 2010, Pages 7602-7604

  Canterbury, Daniel P ^a   Micalizio, Glenn C ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLINGS; ENE-YNE; HOMOALLYLIC ALCOHOL; OXIDATIVE CYCLIZATION; POLYKETIDE ASSEMBLY; REACTION SEQUENCES; REGIO-SELECTIVE; SPIROKETALS; THREE-COMPONENT COUPLING;

ACETYLENE; OLEFINS;

CYCLIZATION;

ACETAL; ALCOHOL; ALKENE; ALKYNE; POLYKETIDE;

ALKYNYLATION; ARTICLE; CHEMISTRY; CROSS COUPLING REACTION; CYCLIZATION; HYDROBORATION;

ALCOHOLS; ALKENES; ALKYNES; CYCLIZATION; FURANS; OXIDATION-REDUCTION; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 77953087696     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja102888f     Document Type: Article

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38. On the basis of a reviewers suggestion, we add that these conditions are typical for thermodynamic control in the stereoselective generation of the spiroacetal. See the Supporting Information for additional details.
39. In each case (eqs 13-16), no evidence was found for the production of stereoisomeric spiroketals. This observation is in accord with the well-established thermodynamic preference for the generation of spiroketals that are stabilized by a double anomeric effect. See the Supporting Information for additional details.