Approach to the synthesis of dolabelides A and B: fragment synthesis by tandem silylformylation-crotylsilylation.
[structure: see text] A synthesis of the C(15)-C(30) fragment of Dolabelides A and B has been achieved. The recently developed asymmetric silane alcoholysis and tandem silylformylation-crotylsilylation reactions were used as the key steps to establish the C(23)-C(27) 1,5-syn-diol. In addition, the flexibility of this methodology has been demonstrated with an efficient synthesis of the C(24)-C(25) trisubstituted olefin.
Schmidt
Darby R
DR
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Park
Peter K
PK
Leighton
James L
JL
D000475:Alkenes / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000440:Butanols / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis*; D005561:Formates / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis; D018942:Macrolides; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D000970:Antineoplastic Agents; D000440:Butanols; D004224:Diterpenes; D005561:Formates; D007659:Ketones; D018942:Macrolides; D012821:Silanes; C481199:dolabelide A; C481200:dolabelide B; C007153:crotonyl alcohol