Total Synthesis of Enantiopure Chabrolonaphthoquinone B Via a Stereoselective Julia-Kocienski Olefination

被引：3

作者：

Rizos, Stergios R. ^{[1
]}

Peitsinis, Zisis, V ^{[1
]}

Koumbis, Alexandros E. ^{[1
]}

机构：

[1] Aristotle Univ Thessaloniki, Dept Chem, Lab Organ Chem, Thessaloniki 54124, Greece

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 15期

关键词：

ENANTIOSELECTIVE SYNTHESIS; ACID; DERIVATIVES; METABOLITES; CONVENIENT; FRAGMENT;

D O I：

10.1021/acs.joc.1c01106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of cytotoxic meroditerpenoid naphthoquinone derivative chabrolonaphthoquinone B (1) in an enantiospecific manner is divulged using a chiral pool approach. The key step of our synthetic route is a modified Julia olefination between a sulfone-bearing aliphatic fragment and a Diels-Alder-derived aromatic aldehyde, leading to the stereoselective construction of the E-trisubstituted double bond.

引用

页码：10440 / 10454

页数：15

共 46 条

[1] SULFURANES .6. REACTIONS INVOLVING ALKOXY LIGANDS OF DIALKOXYDIARYLSULFURANES - FORMATION OF OLEFINS AND ETHERS
ARHART, RJ
MARTIN, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (14) : 5003 - &
[2] Microwave induced selective bromination of 1,4-quinones and coumarins
Bansal, V
Kanodia, S
Thapliyal, PC
Khanna, RN
[J]. SYNTHETIC COMMUNICATIONS, 1996, 26 (05) : 887 - 892
[3] Stereocontrolled synthesis of the C21-C38 fragment of the unnatural enantiomer of the antibiotic nystatin A1
Berkenbusch, T
Brückner, R
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (06) : 1545 - 1557
[4] Blakemore P. R., 2018, Org. React., V95, P1, DOI [10.1002/0471264180.or095.01, DOI 10.1002/0471264180.0R095.01, DOI 10.1002/0471264180.OR095.01]
[5] CATALYTIC HYDROGENATION .5. REACTION OF SODIUM BOROHYDRIDE WITH AQUEOUS NICKEL SALTS - P-1 NICKEL BORIDE, A CONVENIENT, HIGHLY ACTIVE NICKEL HYDROGENATION CATALYST
BROWN, CA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) : 1900 - +
[6] Preparation of Amino-Substituted Indenes and 1,4-Dihydronaphthalenes Using a One-Pot Multireaction Approach: Total Synthesis of Oxybenzo[c]phenanthridine Alkaloids
Calder, Ewen D. D.
McGonagle, Fiona I.
Harkiss, Alexander H.
McGonagle, Grant A.
Sutherland, Andrew
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) : 7633 - 7648
[7] ENANTIOSPECIFIC SYNTHESES OF LEUKOTRIENE-C4, LEUKOTRIENE-D4, AND LEUKOTRIENE-E4 AND [14,15-H-3(2)]LEUKOTRIENE-E4 DIMETHYL ESTER
COHEN, N
BANNER, BL
LOPRESTI, RJ
WONG, F
ROSENBERGER, M
LIU, YY
THOM, E
LIEBMAN, AA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) : 3661 - 3672
[8] Preparations of Anthraquinone and Naphthoquinone Derivatives and Their Cytotoxic Effects
Cui, Xing-Ri
Saito, Ryota
Kubo, Takatsugu
Kon, Daijiro
Hirano, Yuich
Saito, Setsuo
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2011, 59 (03) : 302 - 314
[9] USEFUL DIENE FOR DIELS-ALDER REACTION
DANISHEFSKY, S
KITAHARA, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) : 7807 - 7808
[10] PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES
ECHAVARREN, AM
STILLE, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) : 1557 - 1565

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