Total synthesis of haterumalides NA and NC via a chromium-mediated macrocyclization.
The syntheses of haterumalides NA and NC were accomplished via the macrocyclization of a chlorovinylidene chromium carbenoid onto a pendant aldehyde to generate the C8-C9 bond with the desired stereoisomer as the major product. Utilizing the latter chemistry enables access to both C9 hydroxylated (haterumalides NC and ND) and C9 deoxygenated forms (haterumalides NA, NB, and NE; via deoxygenation of the C9-hydroxyl).
Schomaker
Jennifer M
JM
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Borhan
Babak
B
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D002857:Chromium / Q000737:chemistry; D003500:Cyclization; D005030:Ethylenes / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D005030:Ethylenes; D018942:Macrolides; D009942:Organometallic Compounds; D002857:Chromium; D010100:Oxygen