71686-37-8

Basic information

• Product Name: (3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one
• CAS NO: 71686-37-8
• Molecular Weight: 342.435
• Mol File: 71686-37-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one(71686-37-8)
• EPA Substance Registry System: (3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one(71686-37-8)

Safety Data

• Hazardous Substances Data: 71686-37-8(Hazardous Substances Data)

Upstream product

• 73407-84-8 (3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-octahydro-azuleno[6,5-b]furan-2,4-dione 
• 71686-37-8 (3aα,4α,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>-furan-2(3H)-one 
• 68306-73-0 (1aα,2β,4β,4aβ,7α,7aα,7bα)-1a,2,3,4,4a,7,7a,7b-Octahydro-4,7a-dimethyl-7-(phenylmethoxy)azuleno<4,5-b>oxiren-2-ol 
• 64-19-7 acetic acid 
• 68306-73-0 (1aα,4β,4aβ,7α,7aα,7bα)-1a,2,3,4,4a,7,7a,7b-octahydro-4,7a-dimethyl-7-(phenylmethoxy)azuleno<4,5-b>oxiren-2-ol 
• 100-39-0 benzyl bromide 
• 70913-22-3 (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenol 
• 68241-54-3 (1α,3aβ,4β,8aα)-3a,4,5,8a-Tetrahydro-4,8a-dimethyl-1-(phenylmethoxy)-6(1H)-azulenone 
• 71686-31-2 (1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol 
• 82041-93-8 methyl α,5-dimethyl-4-hydroxy-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate 
• 71748-37-3 (1β,4β,4aα,7β,7aβ)-4,4a,7,7a-tetrahydro-1,4,7a-trimethyl-7-(phenylmethoxy)cyclopentapyran-3(1H)-one 
• 82043-27-4 (1β,4α,4aα,7β,7aβ)-4,4a,7,7a-tetrahydro-1,4,7a-trimethyl-7-(phenylmethoxy)cyclopentapyran-3(1H)-one 
• 82010-17-1 Methanesulfonic acid (3S,3aS,8R,8aR)-3-benzyloxy-3a,8-dimethyl-6-(tetrahydro-pyran-2-yloxy)-3,3a,4,5,6,7,8,8a-octahydro-azulen-4-yl ester 
• 68241-53-2 (3S,3aS,8R,8aR)-3-Benzyloxy-3a,8-dimethyl-6-(tetrahydro-pyran-2-yloxy)-3a,5,6,7,8,8a-hexahydro-3H-azulen-4-one 

Downstream Products

• 73407-87-1 (3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one 
• 73407-84-8 (3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-octahydro-azuleno[6,5-b]furan-2,4-dione 
• 5945-41-5 dl-Mexicanin I 
• 3668-14-2 dl-Linifolin A 
• 71686-37-8 (3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>-furan-2(3H)-one 

Relevant articles and documents

Helenanolides: Stereocontrolled Total Synthesis of dl-Bigelovin, dl-Mexicanin I, and dl-Linifolin A

Stereocontrolled total syntheses of the sesquiterpene lactones dl-bigelovin (11), dl-mexicanin I (12), and dl-linifolin A (13) are described.The syntheses start with the hydroazulenone 4 and proceed via the key epoxy alkohol 9.Elaboration of 9 into the tricyclic γ-lactone 14 dl-bigelovin. α-methylenation.Subsequent oxidation at C(4) completes the synthesis of dl-bigelovin.Epoxide opening of 9 with dilithioacetate provides access to tricyclic lactone 23 which gives way to 24 via reduction of ketone 25.Cleavage of the benzyl ether in 24 followed by α-methylenationand oxidation generates dl-mexicanin I.Acetylation of 12 affords dl-linifolin A.