| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347792 | Tetrahedron: Asymmetry | 2008 | 5 Pages |
A rapid and enantiospecific synthesis of the ABC ring system of tetranortriterpene dumsin and its analogues, starting from the readily available monoterpene (R)-carvone employing two RCM reactions as key steps, is described.
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(10S)-10-Isopropenyl-7-methylspiro[4.5]deca-2,7-dien-6-oneC14H18O[α]D25=-179.2 (c 1.3, CHCl3)Source of chirality: (R)-carvoneAbsolute configuration: (10S)
(10S)-6-Allyl-10-isopropenyl-7-methylspiro[4.5]deca-2,6-dien-8-oneC17H22O[α]D25=+7.8 (c 1.8, CHCl3)Source of chirality: (R)-carvoneAbsolute configuration: (10S)
(6R,7S,10S)-6,7-Bis-allyl-10-isopropenyl-7-methylspiro[4.5]dec-2-en-8-oneC20H28O[α]D20=+13.2 (c 4.8, CHCl3)Source of chirality: (R)-carvoneAbsolute configuration: (6R,7S,10S)
(6R,7R,10S)-6,7-Bis-allyl-10-isopropenyl-7-methylspiro[4.5]dec-2-en-8-oneC20H28O[α]D24=+3.7 (c 1.9, CHCl3)Source of chirality: (R)-carvoneAbsolute configuration: (6R,7R,10S)
(1R,4S,6R)-4-Isopropenyl-1-methylbicyclo[4.4.0]decane-spiro[5,1′]cyclopenta-8,3′-dien-2-oneC18H24O[α]D27=-3.3 (c 0.6, CHCl3)Source of chirality: (R)-carvoneAbsolute configuration: (1R,4S,6R)
(1S,4S,6R)-4-Isopropenyl-1-methylbicyclo[4.4.0]decane-spiro[5,1′]cyclopenta-8,3′-dien-2-oneC18H24O[α]D21=+25.7 (c 2.5, CHCl3)Source of chirality: (R)-carvoneAbsolute configuration: (1S,4S,6R)
