Total synthesis of prostaglandins F1.alpha., E1, F2.alpha., and E2 (natural forms) from a common synthetic intermediate

1970 ◽  
Vol 92 (8) ◽  
pp. 2586-2587 ◽  
Author(s):  
Elias J. Corey ◽  
Ryozi. Noyori ◽  
Thomas K. Schaaf
Keyword(s):  
Total Synthesis ◽  
Natural Forms ◽  
Synthetic Intermediate

An X-Ray Study of the Synthetic Intermediate 9-Cyano-1,10-Dimethyl-6-Ethylenedioxy-1-Octalin

1975 ◽  
Vol 53 (2) ◽  
pp. 192-194 ◽  
Author(s):  
Harry Lynton ◽  
Pik-Yuen Siew
Keyword(s):  
Crystal Structure ◽  
Total Synthesis ◽  
Direct Methods ◽  
Hydrogen Atoms ◽  
Full Matrix ◽  
X Ray ◽  
Ring Junction ◽  
Cell Dimensions ◽  
R Value ◽  
Synthetic Intermediate

The crystal structure of the synthetic intermediate, 9-cyano-1,10-dimethyl-6-ethy]enedioxy-1-octalin, C15H21O2N, was solved by direct methods. The compound crystallizes in the space group p21/c with cell dimensions a = 12.282(4), b = 7.144(3), c = 15.619(5) Å, β = 104.04(1)°. Refinement was carried out isotropically for hydrogen and anisotropically for non-hydrogen atoms using full matrix least squares to an R-value of 0.043 for 1669 observed reflections.This compound, which has a cis configuration at the octalin ring junction, is a precursor to a moiety of the alkaloid thelepogine. The cis conformation is essential for total synthesis of thelopogine by this route.

scholarly journals Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

2014 ◽  
Vol 10 ◽  
pp. 127-133 ◽  
Author(s):  
Andivelu Ilangovan ◽  
Shanmugasundar Saravanakumar
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Biomimetic Approach ◽  
Synthetic Intermediate

A unified strategy was followed for the synthesis of three putrescine bisamides, (+)-grandiamide D, dasyclamide and gigantamide A, isolated from leaves of Aglaia gigantea, by making use of a common synthetic intermediate prepared by the Baylis–Hillman reaction. Asymmetric synthesis of the natural (+)-grandiamide D was accomplished from camphor sultam.

Total Synthesis of Eremophilane-type Sesquiterpenoids: (±)-Eremophilenolide, (±)-Tetrahydroligularenolide, and (±)-Aristolochene

1973 ◽  
Vol 51 (13) ◽  
pp. 2166-2173 ◽  
Author(s):  
Edward Piers ◽  
Michael Bert Geraghty
Keyword(s):  
Total Synthesis ◽  
Keto Acid ◽  
Keto Ester ◽  
Synthetic Intermediate

The total synthesis of the racemic forms of the eremophilane-type sesquiterpenoids eremophilenolide (2), tetrahydroligularenolide (3), and aristolochene (4) is described. The octalone 7 was converted via an efficient, regioselective route into the keto ester 12, which served as a common synthetic intermediate for the preparation of the three sesquiterpenoids. Successive subjection of 12 to alkylation, hydrolysis, and decarboxylation afforded the keto acid 14. Hydrogenation of the latter provided both the cis-fused keto acid 20, which was readily converted into (±)-eremophilenolide (2), and the trans-fused keto acid 15, which was similarly transformed into (±)-tetrahydroligularenolide (3). Conversion of 12 into the dithioketal 23, followed by desulfurization and treatment of the resultant olefinic ester 25 with excess methyllithium, provided the olefinic alcohol 27. Dehydration of the latter yielded (±)-aristolochene (4).

Total synthesis of Δ9(12)-capnellene-8α,10α-diol

1982 ◽  
Vol 23 (52) ◽  
pp. 5471-5474
Author(s):  
G Pattenden
Keyword(s):  
Total Synthesis

Total synthesis of melleumins A and B and their analogs: Determination of stereochemistry and Wnt signal inhibitory activity

Planta Medica ◽  
2008 ◽  
Vol 74 (09) ◽  
Author(s):  
M Ishibashi ◽  
S Hanazawa ◽  
Y Uchino ◽  
X Li ◽  
MA Arai
Keyword(s):  
Total Synthesis ◽  
Inhibitory Activity ◽  
Wnt Signal
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