The dihydrofuran template approach to furofuran synthesis.
Flash vacuum pyrrolysis of vinyl epoxides provides cis-dihydrofuran carboxylic esters in good yields and diastereoselectivities, which, on base-promoted epimerisation afford the complementary trans series. The compounds provide a viable template for a Lewis acid promoted cyclisation to provide the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane core found in the furofuran series of natural lignans. This strategy is stereodivergent and can be controlled to provide the exo-exo, exo-endo or endo-endo stereochemistries. The approach has been exemplified in syntheses of the sesamyl furofurans (+/-)-epiasarinin and (+/-)-asarinin.
Aldous
David J
DJ
Sanofi-Aventis Pharma Inc, Bridgewater, New Jersey 08807, USA.
Batsanov
Andrei S
AS
Yufit
Dmitrii S
DS
Dalençon
Anne J
AJ
Dutton
William M
WM
Steel
Patrick G
PG
D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D013058:Mass Spectrometry
D005663:Furans