Stereochemical diversity through cyclodimerization: synthesis of polyketide-like macrodiolides.
[reaction: see text] An expeditious procedure for the direct formation of stereochemically well-defined macrodiolides is described. Cyclodimerizations of enantioenriched C7 and C8 hydroxy esters 6 in the presence of catalytic amounts of distannoxane transesterification catalysts afford 14- to 22-membered macrodiolides 7-9 bearing up to six stereocenters. Additional structural diversity is introduced by further stereoselective reactions on selected macrodiolides 7a, 7g, 10a, and 11.
Su
Qibin
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Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Beeler
Aaron B
AB
Lobkovsky
Emil
E
Porco
John A
JA
Panek
James S
JS
D002384:Catalysis; D003500:Cyclization; D019281:Dimerization; D004951:Esterification; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D018942:Macrolides