Synthesis of the bryostatin 1 northern hemisphere (C1-C16) via desymmetrization by ketalization/ring-closing metathesis.
[reaction: see text] Synthesis of the northern hemisphere (C1-C16) of bryostatin 1, a potent anticancer agent, has been accomplished in 14 steps and 11% overall yield via desymmetrization by ketalization/ring-closing metathesis. A 2,9-dioxabicyclo[3.3.1]nonane template facilitated stereoselective A-ring functionalization, while an efficient hetero-Diels-Alder reaction was used to elaborate the B-ring.
Voight
Eric A
EA
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1396, USA.
Seradj
Hassan
H
Roethle
Paul A
PA
Burke
Steven D
SD
D000080:Acetals / Q000737:chemistry*; D000473:Alkanes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D054713:Bryostatins; D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis*; D015394:Molecular Structure
D000080:Acetals; D000473:Alkanes; D000970:Antineoplastic Agents; D001643:Bridged Bicyclo Compounds; D054713:Bryostatins; D018942:Macrolides; C046785:bryostatin 1; C017573:nonane