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

Base Information

• Chemical Name: Azuleno[4,5-b]furan-2(3H)-one,3a,4,5,6,6a,7,9a,9b-octahydro-3,9-dimethyl-6-methylene-, (3S,3aS,6aR,9aR,9bS)-
• CAS No.: 38236-17-8
• Molecular Formula: C15H20 O2
• Molecular Weight: 232.323
• Mol file: 38236-17-8.mol

Synonyms:Azuleno[4,5-b]furan-2(3H)-one,3a,4,5,6,6a,7,9a,9b-octahydro-3,9-dimethyl-6-methylene-, [3S-(3a,3aa,6aa,9aa,9bb)]-; (11S)-Guaia-3,10(15)-dieno-12,6a-lactone; Isocostuslactone

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

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 33 articles about Azuleno[4,5-b]furan-2(3H)-one,3a,4,5,6,6a,7,9a,9b-octahydro-3,9-dimethyl-6-methylene-, (3S,3aS,6aR,9aR,9bS)- 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: 95.0%

(3S,3aS,6R,6aR,9aR,9bS)-6-Hydroxy-3,6,9-trimethyl-3a,4,5,6,6a,7,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one (17946-95-1) → isocostus lactone (38236-17-8)

Guidance literature:

(3S,3aS,6R,6aR,9aR,9bS)-6-Hydroxy-3,6,9-trimethyl-3a,4,5,6,6a,7,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one; With 1,4-diaza-bicyclo[2.2.2]octane; In tetrahydrofuran; Inert atmosphere;

With thionyl chloride; In tetrahydrofuran; at -78 ℃; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol101705j

Reference yield: 72.0%

(11S)-3α-(mesyloxy)-4βH-guai-10(14)-en-13,6α-lactone (82207-06-5) → isocostus lactone (38236-17-8)

Guidance literature:

With lithium carbonate; lithium bromide; In N,N-dimethyl-formamide; at 110 - 115 ℃; for 1.5h;

DOI:10.1021/jo00141a020

Reference yield: 48.5%

4α-hydroxy-1α,5α,6β,7α,11α-H-guaian-10(15)-en-6,12-olide (68421-48-7) → isocostus lactone (38236-17-8)

Guidance literature:

With thionyl chloride; In pyridine; at 0 ℃; for 0.25h;

DOI:10.1016/0040-4020(80)80216-X

upstream raw materials:

Methyltriphenylphosphonium bromide

(3S,3aS,6aS,9R,9aS,9bS)-9-Hydroxy-3,9-dimethyl-decahydro-azuleno[4,5-b]furan-2,6-dione

(11S)-3α-(mesyloxy)-4βH-guai-10(14)-en-13,6α-lactone

gallicin

Downstream raw materials:

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

(+)-3α,4α-epoxy-1,5,7αH,6,11βH-guai-1(14)-en-6,12-olide

isodehydrocostus lactone

C₁₅H₁₈O₃

Refernces

• 1、 Yuuya, Saori,Hagiwara, Hisahiro,Suzuki, Toshio,Ando, Masayoshi,Yamada, Atsushi,Suda, Kouji,Kataoka, Takao,Nagai, Kazuo. "Guaianolides as immunomodulators. Synthesis and biological activities of dehydrocostus lactone, mokko lactone, eremanthin, and their derivatives". . p. 22 - 30. Retrieved 2007/10/03.
• 2、 Delair, Philippe,Kann, Nina,Greene, Andrew E.. "Synthesis (in ent-form) of a Novel Jalcaguaianolide from Ferula arrigonii Bocchieri". . p. 1651 - 1652. Retrieved 2007/10/02.