(3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

Base Information

Chemical Name:(3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
CAS No.:90807-54-8
Molecular Formula:C₁₅H₂₀O₂
Molecular Weight:232.323
Hs Code.:

Synonyms:(3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

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Chemical Property of (3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

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Technology Process of (3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

There total 1 articles about (3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 9.0%

: 90807-53-7
1β-Mesyloxyeudesm-4(14)-eno-13,6α-lactone

: 38236-17-8
isocostus lactone

: 4955-03-7
11β,13-dehydrocostuslactone

: 90807-54-8
(3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

: (3S,3aS,6aR,9aR,9bS)-3,6-Dimethyl-9-methylene-3a,4,6a,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

Guidance literature:: With potassium acetate; In acetic acid; for 22h; Further byproducts given. Yields of byproduct given; Heating;
DOI:10.1021/np980092u

Reference yield:

: 90807-54-8
(3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

: 219825-02-2
1β,10β-epoxy-11α-(phenylseleno)guaia-4(14)-eno-13,6α-lactone

Guidance literature:: Multi-step reaction with 2 steps

1: 44 percent / m-CPBA / CHCl₃ / 1 h / 0 °C

2: 1.) LDA, 2.) HMPA / 1.) THF, -76 deg C, 1 h, 2.) THF, -76 deg C, 30 min and -40 deg C, 1 5 h.

With N,N,N,N,N,N-hexamethylphosphoric triamide; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In chloroform;
DOI:10.1021/np980092u

Reference yield:

: 90807-54-8
(3S,3aS,9aS,9bS)-3,6-Dimethyl-9-methylene-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

: 219825-03-3
1β,10β-epoxy-11β-(phenylseleno)guaia-4(14)-eno-13,6α-lactone

Guidance literature:: Multi-step reaction with 2 steps

1: 44 percent / m-CPBA / CHCl₃ / 1 h / 0 °C

2: 1.) LDA, 2.) HMPA / 1.) THF, -76 deg C, 1 h, 2.) THF, -76 deg C, 30 min and -40 deg C, 1 5 h.

With N,N,N,N,N,N-hexamethylphosphoric triamide; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In chloroform;
DOI:10.1021/np980092u