Synthesis of the C16-C28 spiroketal subunit of spongistatin 1 (altohyrtin A): the pyrone approach.
The synthesis of the CD spiroketal fragment of spongistatin 1 (altohyrtin A) has been accomplished utilizing the addition of a metalated pyrone to an aldehyde and subsequent acid-catalyzed spirocyclization. A stereoselective hydrogenation and subsequent conformational inversion establish the C19 stereocenter and the axial-equatorial spiroketal center.
Crimmins
M T
MT
Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill 27599-3290, USA. crimmins@email.unc.edu
Katz
J D
JD
D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides; D008968:Molecular Conformation; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism; D000095702:Polyether Toxins
D000447:Aldehydes; D000970:Antineoplastic Agents; D004988:Ethers, Cyclic; D007783:Lactones; D018942:Macrolides; D011753:Pyrones; C083856:spongistatin 1; D000095702:Polyether Toxins