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Synthesis of Hexacyclo(5.4.0.0(2,6).0(3,10).0(5,9).0(8,11)undecane-8-carboxylic Acid) (Homopentaprismane-8-carboxylic Acid).

ADA214973

Publication Date	1989
Personal Author	Marchand, A. P.; Deshpande, M. N.
Page Count	6
Abstract	The title compound was synthesized in nine steps from pentacyclo(5.4 .0.0(2,6).0(3,10).0(5,9))- undecane-8, 11-dione monoethylene ketal (2) in 23% overall yield. Thus, reaction of 2 with ethyl (diethoxyphosphinyl) acetate in the presence of NaH provided the corresponding 8-carboethoxymethylene derivative (3, 93%). The corresponding endo-11-carboethoxy-methylene derivative (4, 100%) was prepared via catalytic hydrogenation of 3. Hydrolysis of the ester and ketal groups in 4 with aqueous acid gave 5 (90%). The corresponding substituted 1,3-dishomopentaprismane (6,91%) was synthesized by subsequent reaction of 5 with NaH/DMF-THF. Reaction of 6 with MeLi/THF gave 7 (80%), which, upon oxidation with CF3CO3H followed by workup with aqueous base afforded the corresponding 1,3-bishomo-pentaprismanediol (8, 60%). Organic chemistry.
Keywords	Carboxylic acids Synthesis(Chemistry) Esters Hydrolysis Organic chemistry Oxidation Water Cyclic compounds Decanes Sodium compounds Hydrides Ethylene Ketones Ethyl radicals Oxygen Phosphine Acetates Methylenes Chemical derivatives Catalysis Hydrogenation Formamides Methyl radicals Furans Hydrogen compounds Reprints Hexacyclourdecane Chemical reaction mechanisms Undecanes Prismanes Hexacyclic Compounds Diones Diols Sodium Hydride Carboxylic acid
Source Agency	Air Force Non Paid Reprints
NTIS Subject Category	99D - Basic & Synthetic Chemistry 99F - Physical & Theoretical Chemistry
Corporate Authors	North Texas State Univ., Denton. Dept. of Chemistry.; Air Force Office of Scientific Research, Bolling AFB, DC.
Supplemental Notes	Pub. in Jnl. of Organic Chemistry, v54 n13 p3226-3229 1989.
Document Type	Journal Article
NTIS Issue Number	199006

Synthesis of Hexacyclo(5.4.0.0(2,6).0(3,10).0(5,9).0(8,11)undecane-8-carboxylic Acid) (Homopentaprismane-8-carboxylic Acid).

Synthesis of Hexacyclo(5.4.0.0(2,6).0(3,10).0(5,9).0(8,11)undecane-8-carboxylic Acid) (Homopentaprismane-8-carboxylic Acid).
ADA214973

Publication Date	1989
Personal Author	Marchand, A. P.; Deshpande, M. N.
Page Count	6
Abstract	The title compound was synthesized in nine steps from pentacyclo(5.4 .0.0(2,6).0(3,10).0(5,9))- undecane-8, 11-dione monoethylene ketal (2) in 23% overall yield. Thus, reaction of 2 with ethyl (diethoxyphosphinyl) acetate in the presence of NaH provided the corresponding 8-carboethoxymethylene derivative (3, 93%). The corresponding endo-11-carboethoxy-methylene derivative (4, 100%) was prepared via catalytic hydrogenation of 3. Hydrolysis of the ester and ketal groups in 4 with aqueous acid gave 5 (90%). The corresponding substituted 1,3-dishomopentaprismane (6,91%) was synthesized by subsequent reaction of 5 with NaH/DMF-THF. Reaction of 6 with MeLi/THF gave 7 (80%), which, upon oxidation with CF3CO3H followed by workup with aqueous base afforded the corresponding 1,3-bishomo-pentaprismanediol (8, 60%). Organic chemistry.
Keywords	Carboxylic acids Synthesis(Chemistry) Esters Hydrolysis Organic chemistry Oxidation Water Cyclic compounds Decanes Sodium compounds Hydrides Ethylene Ketones Ethyl radicals Oxygen Phosphine Acetates Methylenes Chemical derivatives Catalysis Hydrogenation Formamides Methyl radicals Furans Hydrogen compounds Reprints Hexacyclourdecane Chemical reaction mechanisms Undecanes Prismanes Hexacyclic Compounds Diones Diols Sodium Hydride Carboxylic acid
Source Agency	Air Force Non Paid Reprints
NTIS Subject Category	99D - Basic & Synthetic Chemistry 99F - Physical & Theoretical Chemistry
Corporate Authors	North Texas State Univ., Denton. Dept. of Chemistry.; Air Force Office of Scientific Research, Bolling AFB, DC.
Supplemental Notes	Pub. in Jnl. of Organic Chemistry, v54 n13 p3226-3229 1989.
Document Type	Journal Article
NTIS Issue Number	199006