Stereoselective total synthesis of (+)-oploxyne A, (-)-oploxyne B, and their C-10 epimers and structure revision of natural oploxyne B

Journal of Organic Chemistry

Volumn 76, Issue 8, 2011, Pages 2568-2576

  Yadav, J S ^a,b   Boyapelly, Kumaraswamy ^a   Alugubelli, Sathish Reddy ^a   Pabbaraja, Srihari ^a   Vangala, Janakiram R ^a   Kalivendi, Shasi V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENIC ALCOHOLS; CROSS COUPLING REACTIONS; DIACETYLENES; EPIMERS; NEUROBLASTOMAS; PROSTATE CANCER CELLS; STEREO-SELECTIVE; TARGET COMPOUND; TOTAL SYNTHESIS;

ACETYLENE; CARBOHYDRATES; CELL CULTURE; CHLORINE COMPOUNDS; DISEASES; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

1 [(1 BROMOPENT 1 YN 3 YLOXY)METHYL] 4 METHOXYBENZENE; 1 [5 [5 (4 METHOXYBENZYLOXY)HEPTA 1,3 DIYNYL] 2,2 DIMETHYL 1,3 DIOXOLAN 4 YL] OCTYL 4 METHYLBENZENESULFONATE; 1 [5 [5 (4 METHOXYBENZYLOXY)HEPTA 1,3 DIYNYL] 2,2 DIMETHYL 1,3 DIOXOLAN 4 YL]OCTAN 1 OL; 1 [5 ETHYNYL 2,2 DIMETHYL 1,3 DIOXOLAN 4 YL] OCTAN 1 OL; 2 [ 6 (HYDROXYMETHYL) 2,2 DIMETHYLTETRA HYDROFURO (3,4 DEXRO)(1,3)DIOXOL 4 YL]ACETALDEHYDE; 2 [6 (HYDROXYMETHYL) 2,2 DIMETHYLTETRAHYDROFURO (3,4 DEXTRO) (1,3)DIOXOL 4 YL]ACETALDEHYDE; 2 [6 (HYDROXYMETHYL) 2,2 DIMETHYLTETRAHYDROFUROL (3,4 DEXTRO) (1,3)DIOXOL 4 YL]ACETALDEHYDE; 2 [6 (HYDROXYMETHYL) 2,2 DIMETHYLTETRAHYDROFUROL (3,4 DEXTRO)(1,3)DIOXOL 4 YL]ACETALDEHYDE; 3 (4 METHOXYBENZYLOXY)PENTANE 1,2 DIOL; 4 (CHLOROMETHYL) 6 HEPTYL 2,2 DIMETHY LTETRAHYDROFURO (3,4 DEXTRO)(1,3)DIOXOLE; 4 (CHLOROMETHYL) 6 HEPTYL 2,2-DIMETHY 4 (CHLOROMETHYL) 6 HEPTYL 2,2 DIMETHYLTETRAHYDROFURO(3,4 DEXTRO) (1,3) DIOXOLE; 4 [5 (4 METHOXYBENZYLOXY)HEPTA 1,3 DIYNYL] 5 [1 METHOXYOCTYL] 2,2 DIMETHYL 1,3 DIOXOLANE; 4 ETHYNYL 5 (1 METHOXYOCTYL) 2,2 DIMETHYL 1,3 DIOXOLANE; 4 ETHYNYL 5 (1 METHOXYOCTYL) 2,2 DIMETHYL 1,3 DLIOXOLANE; 7 [5 (1 METHOXYOCTYL) 2,2 DIMETHYL 1,3 DIOXOLAN 4 YL]HEPTA 4,6 DIYN 3 OL; [ 6 (HEPT 2 ENYL) 2,2 DIMETHYLTETRAHYDROFURO(3,4 DDXTRO) (1,3)DIOXOL 4 YL]METHANOL; [6 (HEPT 2 ENYL) 2,2 DIMETHYLTETRAHYDROFURO(3,4 DEXTRO) (1,3) DIOXOL 4 YL METHANOL; [6 HEPTYL 2,2 DIMETHYLTETRAHYDROFURO (3,4 DEXTRO) (1,3) DIOXOL 4, YL] METHANOL; [6 HEPTYL 2,2 DIMETHYLTETRAHYDROFURO (3,4 DEXTRO)(1,3)DIOXOL 4 YL] METHANOL; ANTINEOPLASTIC AGENT; C 10 EPIMER OPLOXYNE A; C 10 EPIMER OPLOXYNE B; DOXORUBICIN; ETHYL 2 [6 (HYDROXYMETHYL) 2,2 DIMETHY LTETRAHYDROFURO(3,4 DEXTRO)(1,3)DIOXOL 4 YL]ACETATE; ETHYL 2 [6 (HYDROXYMETHYL) 2,2 DIMETHYLTETRAHYDROFUROL (3,4 DEXRO)(1,3)DIOXOL 4 YL]ACETATE; OPLOXYNE A; OPLOXYNE B; PANAXYDOL; PANAXYTRIOL; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CELL STRAIN MCF 7; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMER; HUMAN; HUMAN CELL; IC 50; LUNG CANCER; NEUROBLASTOMA CELL; PROSTATE CANCER;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CATALYSIS; CELL LINE, TUMOR; DOXORUBICIN; FEMALE; HUMANS; LUNG NEOPLASMS; MALE; MOLECULAR STRUCTURE; NEUROBLASTOMA; POLYACETYLENES; PROSTATIC NEOPLASMS; STEREOISOMERISM;

EID: 79953884039     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102445h     Document Type: Article

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