Progress toward the total synthesis of saudin: Development of a tandem Stille-oxa-electrocyclization reaction

Organic Letters

Volumn 7, Issue 12, 2005, Pages 2413-2416

  Tambar, Uttam K ^a   Kano, Taichi ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIDIABETIC AGENT; DITERPENOID; PALLADIUM COMPLEX; PYRAN DERIVATIVE; SAUDIN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; STILLE REACTION;

CYCLIZATION; DITERPENES; FURANS; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC; PYRANS; STEREOISOMERISM;

EID: 20544471448     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050705b     Document Type: Article

References (19)

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19. Toward this end, we have encountered some level of difficulty implementing the three component coupling chemistry outlined in Scheme 1. In particular C-C bond formation at the sterically congested C(16) center has been difficult. We are currently developing catalytic asymmetric methods to synthesize hindered quaternary carbon centers, and plan to apply these strategies to override any inherent steric and stereochemical bias of the pyran systems prepared in this study. For an example, see: Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 15044-15045.