An approach to pancratistatins via ring-closing metathesis: efficient synthesis of novel 1-aryl-1-deoxyconduritols F. cv.
Structurally novel cyclitols, 1-aryl-1-deoxyconduritols F, were efficiently prepared from d-xylose, utilizing RCM as a key step. Various aromatic residues were incorporated in the cyclitol skeleton with total stereochemical control, utilizing a diastereoselective aryl cuprate addition to a gamma-alkoxy enoate. The synthetic route establishes a firm foundation for a practical synthesis of the antitumor alkaloid pancratistatin and its aryl analogues. [structure: see text]
Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA.
Oleg N
ON
Nadein
Alexander
A
Kornienko
D047151:Amaryllidaceae Alkaloids; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D003500:Cyclization; D005960:Glucosides / Q000737:chemistry*; D007546:Isoquinolines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014994:Xylose / Q000737:chemistry
D047151:Amaryllidaceae Alkaloids; D000970:Antineoplastic Agents; D005960:Glucosides; D007546:Isoquinolines; C417483:conduritol F; C044997:pancratistatin; D014994:Xylose