70913-22-3

Upstream product

• 100-39-0 benzyl bromide 
• 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 
• 82043-29-6 methyl α,5-dimethyl-4-(phenylmethoxy)-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate 
• 82010-16-0 (3S,3aR,8R,8aR)-3-Benzyloxy-3a,8-dimethyl-6-(tetrahydro-pyran-2-yloxy)-3,3a,4,5,6,7,8,8a-octahydro-azulen-4-ol 
• 82010-19-3 Methanesulfonic acid (3S,3aS,8R,8aR)-3-benzyloxy-3a,8-dimethyl-6-oxo-3,3a,4,5,6,7,8,8a-octahydro-azulen-4-yl ester 
• 82010-18-2 Methanesulfonic acid (3S,3aS,8R,8aR)-3-benzyloxy-6-hydroxy-3a,8-dimethyl-3,3a,4,5,6,7,8,8a-octahydro-azulen-4-yl ester 
• 68241-51-0 1-[(1S,2S,5S)-2-Benzyloxy-5-((E)-(S)-3-methoxy-1-methyl-allyl)-1-methyl-cyclopent-3-enyl]-ethanone 
• 71686-33-4 (3S,3aS,8R,8aR)-3-Benzyloxy-6-hydroxy-3a,8-dimethyl-3a,5,6,7,8,8a-hexahydro-3H-azulen-4-one 
• 82010-14-8 (R)-2-[(1S,4S,5R)-4-Benzyloxy-5-((S)-1-hydroxy-ethyl)-5-methyl-cyclopent-2-enyl]-propionic acid methyl ester 
• 82043-30-9 α,5-dimethyl-4-(phenylmethoxy)-5-(1-hydroxyethyl)-2-cyclopentene-1-acetic acid 

Downstream Products

• 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 
• 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 
• 71686-37-8 (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 
• 68241-55-4 (1aα,4β,4aβ,7α,7aα,7bα)-3,4,4a,7,7a,7b-hexahydro-4,7a-dimethyl-7-(phenylmethoxy)azuleno<4,5-b>oxiren-2(1aH)-one 

Relevant academic research and scientific papers

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.

Pseudoguaianolides. 2. Stereocontrolled Total Synthesis of the Helenanolide dl-Helenalin

A stereocontrolled total synthesis of the sesquiterpene lactone dl-helenalin (2) is described.The synthesis starts with cyclopentenol 3 and proceeds via the intermediacy of perhydroazulenone 20.Elaboration of 20 into epoxy alcohol 28 sets the stage for in