Strigillanoic acid B

Base Information

• Chemical Name: Strigillanoic acid B
• CAS No.: 34327-14-5
• Molecular Formula: C20H28O3
• Molecular Weight: 316.43452
• Mol file: 34327-14-5.mol

Synonyms:

Chemical Property of Strigillanoic acid B

Chemical Property:

• PSA: 50.44000
• LogP: 5.07570

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Strigillanoic acid B

There total 15 articles about Strigillanoic acid B 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:

(+/-)-(4aα,5α,6β)-5-ethenyl-4,4a,5,6,7,8-hexahydro-1,5,6-trimethyl-2(1H)-naphthalenone (89295-92-1,90122-67-1,112420-63-0) → (+/-)-maingayic acid (19902-42-2,34327-14-5,50489-83-3,89362-70-9,90192-31-7,134002-11-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 83 percent / benzene; toluene / 1.5 h / 30 - 35 °C

2: camphorsulphonic acid / benzene

3: 1) B₂H₆, 2) H₂O₂, NaOH / 1) THF

4: DMSO, (COCl)2 / CH₂Cl₂

5: 2) pyridine / 1) Et₂O

6: Li / liquid ammonia / -78 °C

7: 2 M HCl / acetone / 1.5 h / Ambient temperature

8: 1) LiB(CHMeEt)3H, 2) POCl₃ / 1) THF, -78 deg C, 2) pyridine, r.t., overnight

9: 1) iBu₂AlH, 2) AcOH / 1) toluene, 0 deg C, 1.5 h, 2) THF, H₂O, 100 deg C, 2 h

10: NaClO₂, NaH₂PO₄, Me₂C=CHMe / 2-methyl-propan-2-ol; H₂O / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; dihydrogen peroxide; lithium; L-Selectride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; diborane; trichlorophosphate; In dichloromethane; ammonia; water; acetone; toluene; tert-butyl alcohol; benzene;

DOI:10.1039/c39830001516

Reference yield:

(+/-)-3,4,4aβ,5,6,7,8,8a-octahydro-8aα-cyano-1α,5α,6α-trimethyl-5β-vinyl-2(1H)-naphthalenone (89295-93-2,90122-79-5) → (+/-)-maingayic acid (19902-42-2,34327-14-5,50489-83-3,89362-70-9,90192-31-7,134002-11-2)

Guidance literature:

Multi-step reaction with 9 steps

1: camphorsulphonic acid / benzene

2: 1) B₂H₆, 2) H₂O₂, NaOH / 1) THF

3: DMSO, (COCl)2 / CH₂Cl₂

4: 2) pyridine / 1) Et₂O

5: Li / liquid ammonia / -78 °C

6: 2 M HCl / acetone / 1.5 h / Ambient temperature

7: 1) LiB(CHMeEt)3H, 2) POCl₃ / 1) THF, -78 deg C, 2) pyridine, r.t., overnight

8: 1) iBu₂AlH, 2) AcOH / 1) toluene, 0 deg C, 1.5 h, 2) THF, H₂O, 100 deg C, 2 h

9: NaClO₂, NaH₂PO₄, Me₂C=CHMe / 2-methyl-propan-2-ol; H₂O / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; dihydrogen peroxide; lithium; L-Selectride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; diborane; trichlorophosphate; In dichloromethane; ammonia; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1039/c39830001516

Reference yield:

methyl propanoyl acetate (30414-53-0) → (+/-)-maingayic acid (19902-42-2,34327-14-5,50489-83-3,89362-70-9,90192-31-7,134002-11-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) NaOMe, 2.) 2M HCl / 1.) MeOH, benzene, RT, 30 min; 2.) MeOH, RT, 15 h and reflux, 7 h

2: 83 percent / benzene; toluene / 2 h / 28 - 35 °C

3: 93 percent / p-toluenesulfonic acid / benzene / 7 h / Heating; water formed was removed by the use Dean-Stark apparatus.

4: 1.) 0.8M diborane, 2.) 30percent H₂O₂, 2M NaOH / 1.) THF, RT, 3 h, 2.) 3 h

5: 75.5 percent / CrO₃, pyridine / CH₂Cl₂ / 3 h

6: 1.) n-butyllithium / 1.) ether, hexane, 2.) -78 deg C, 1 h

7: pyridine / Ambient temperature

8: Li, liq. NH₃ / tetrahydrofuran / 0.25 h / -78 °C

9: 2M HCl / acetone / 1.5 h / Ambient temperature

10: 1.) 1M L-Selectride in THF, 2.) 30percent H₂O₂, 2M NaOH / 1.) THF, -78 deg C, 1 h, 2.) RT

11: phosphorus oxychloride, pyridine / 2 h / Ambient temperature

12: 94 percent / diisobutylaluminium hydride / toluene / 2 h / Ambient temperature

13: NaClO₂, NaH₂PO₄, tert-amylene / butan-1-ol; H₂O / 20 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; ammonia; dihydrogen peroxide; sodium methylate; lithium; L-Selectride; diisobutylaluminium hydride; 2-Methyl-1-butene; diborane; trichlorophosphate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; acetone; toluene; butan-1-ol; benzene;

DOI:10.1016/S0040-4020(01)90099-7

upstream raw materials:

(+/-)-15,16-epoxy-19-oxo-trans-cleroda-3,13⁽¹⁶⁾,14-triene

3,4-dimethyl-cyclohex-2-enone

(+/-)-(4aα,5α,6β)-5-ethenyl-4,4a,5,6,7,8-hexahydro-1,5,6-trimethyl-2(1H)-naphthalenone

(+/-)-3,4,4aβ,5,6,7,8,8a-octahydro-8aα-cyano-1α,5α,6α-trimethyl-5β-vinyl-2(1H)-naphthalenone

Refernces

• 1、 Tokoroyama, Takashi,Fujimori, Kaoru,Shimizu, Takayoshi,Yamagiwa, Yoshiro,Monden, Mitsugu,Iio, Hideo. "A Versatile Method for the Synthesis of Clerodane Diterpenoids: Synthesis of cis and trans Representatives". . p. 1516 - 1518. Retrieved 2007/10/02.