Total synthesis of cis-sylvaticin.
An asymmetric total synthesis of (+)-cis-sylvaticin is described. Key steps include the use of permanganate-mediated oxidative cyclization of 1,5-dienes to synthesize the two major fragments 2 and 3 and a catalytically efficient tethered RCM to unite these THF-containing fragments. In addition, t-BuP 4 base was found to reliably promote rapid alkylation of the butenolide precursor fragment 4.
Brown
Lynda J
LJ
School of Chemistry, University of Southampton, Highfield, Southampton, UK.
Spurr
Ian B
IB
Kemp
Stephen C
SC
Camp
Nicholas P
NP
Gibson
Karl R
KR
Brown
Richard C D
RC
D015107:4-Butyrolactone / Q000737:chemistry; D000478:Alkylation; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D011090:Polyenes / Q000737:chemistry*; D031045:Rollinia / Q000737:chemistry; D013237:Stereoisomerism
D005663:Furans; D011090:Polyenes; C063434:sylvaticin; D015107:4-Butyrolactone