Base Catalyzed Isomerization of Epoxides to Bicyclic Allylic Alcohols, Potential Intermediates for the Total Synthesis of the DL-Aldohexoses

1974 ◽  
Vol 52 (6) ◽  
pp. 988-992 ◽  
Author(s):  
Kurupati Ranganayakulu ◽  
Udai P. Singh ◽  
Thomas P. Murray ◽  
Robert K. Brown
Keyword(s):  
Total Synthesis ◽  
Allylic Alcohols ◽  
Lithium Diethylamide

Treatment of the epoxide 2-deoxy-1,6:3,4-dianhydro-β-DL-ribo-hexopyranose (3) with n-butyllithium, and the epoxides 2-deoxy-1,6:3,4-dianhydro-β-DL-lyxo-hexopyranose (5) and 4-deoxy-1, 6:2,3-dianhydro-β-DL-lyxo-hexopyranose (7) with lithium diethylamide has provided 1,6-anhydro-2,3-dideoxy-β-DL-erythro-hex-2-enopyranose (4), 1,6-anhydro-2,3-dideoxy-β-DL-threo-hex-2-enopyranose (6), and 1,6-anhydro-3,4-dideoxy-β-DL-threo-hex-3-enopyranose (8) in yields of 65, 50, and 20%, respectively. These allylic alcohols are potential intermediates for the synthesis of the various DL-aldohexoses.

ChemInform Abstract: BASE CATALYZED ISOMERIZATION OF EPOXIDES TO BICYCLIC ALLYLIC ALCOHOLS, POTENTIAL INTERMEDIATES FOR THE TOTAL SYNTHESIS OF DL-ALDOHEXOSES

1974 ◽  
Vol 5 (23) ◽  
pp. no-no
Author(s):  
KURUPATI RANGANAYAKULU ◽  
UDAI P. SINGH ◽  
THOMAS P. MURRAY ◽  
ROBERT K. BROWN
Keyword(s):  
Total Synthesis ◽  
Allylic Alcohols

scholarly journals Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene

2016 ◽  
Vol 12 ◽  
pp. 1361-1365 ◽  
Author(s):  
Frederick J Seidl ◽  
Noah Z Burns
Keyword(s):  
Total Synthesis ◽  
Allylic Alcohols ◽  
Critical Factors

The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (−)-anverene.

Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids

2017 ◽  
Vol 53 (13) ◽  
pp. 2170-2173 ◽  
Author(s):  
Nivesh Kumar ◽  
Mrinal Kanti Das ◽  
Santanu Ghosh ◽  
Alakesh Bisai
Keyword(s):  
Total Synthesis ◽  
Allylic Alcohols ◽  
Claisen Reaction

Pd(0)-Catalyzed deacylative allylation (DaA) of 2-oxindoles sharing acyl functionality at 3-position with allylic alcohols via retro-Claisen reaction has been reported.

Formal Total Synthesis of (+)-Citrafungin A

2009 ◽  
Vol 62 (7) ◽  
pp. 676 ◽  
Author(s):  
Sammi Tsegay ◽  
Helmut Hügel ◽  
Mark A. Rizzacasa
Keyword(s):  
Total Synthesis ◽  
Butyl Ester ◽  
Allylic Alcohols ◽  
Key Steps

The formal total synthesis of the fungal GGTase I inhibitor (+)-citrafungin A 1 is described. The key steps include a selective vinyl anion addition of the anion derived from iodide 10 to the lactone 9 and lactonization/selective deprotection of the allylic alcohols 8 and 23 to afford the citrafungin lactone. Esterification with the isocitrate 6 afforded citrafungin A tetra-t-butyl ester 5 which completed the formal total synthesis.

Stereoselective anti-SN2′-Substitutions of Secondary Alkylcopper-Zinc Reagents with Allylic Epoxides: Total Synthesis of (3S,6R,7S)-Zingiberenol

Synthesis ◽  
2019 ◽  
Vol 52 (06) ◽  
pp. 873-881 ◽  
Author(s):  
Juri Skotnitzki ◽  
Alexander Kremsmair ◽  
Bilal Kicin ◽  
Rakan Saeb ◽  
Vincent Ruf ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Allylic Alcohols ◽  
Alkyl Iodides

Chiral secondary mixed alkylcopper-zinc reagents were prepared from the corresponding alkyl iodides and reacted with allylic epoxides via an anti-SN2′-substitution and retention of configuration of the chiral alkylorganometallic, leading to chiral allylic alcohols. This method was used in a total synthesis of the natural product (3S,6R,7S)-zingiberenol in 8 steps and 9.7% overall yield [dr (3S,6R) = 99:1; dr (6R,7S) = 81:19] starting from commercially available 3-methyl-2-cyclohexenone.

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