Total Synthesis of the Potent cAMP Signaling Agonist (-)-Alotaketal

被引：39

作者：

Huang, Jinhua ^{[2
]}

Yang, Jessica R. ^{[1
]}

Zhang, Jin ^{[1
]}

Yang, Jiong ^{[2
]}

机构：

[1] Johns Hopkins Univ, Sch Med, Dept Pharmacol & Mol Sci, Baltimore, MD 21205 USA

[2] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 21期

关键词：

STEREOSELECTIVE-SYNTHESIS; SECONDARY ALCOHOLS; HYPOCHLOROUS ACID; ESTERS; CONVERSION; CHLORIDES; REDUCTION; ALDEHYDES; REAGENTS; KETONES;

D O I：

10.1021/ja303529z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed a convergent synthetic route to the potent cAMP signaling agonist (-)-alotaketal A that employs two stages of SmI2-mediated reductive allylation reactions for assembling the polycycle and fragment coupling. Also notable are a Hg(OAc)(2)-mediated selective alkene oxidation and the subtlety of the formation of the unprecedented spiroketal ring system. The probes AKAR4 and ICUE3 were used to evaluate the cAMP singaling agonistic activity of (-)-alotaketal A and elucidate its structure-activity relationship.

引用

页码：8806 / 8809

页数：4

共 37 条

[1] Stereoselective synthesis of acetoacetate-derived enol triflates [J].

Babinski, David ;

Soltani, Omid ;

Frantz, Doug E. .

ORGANIC LETTERS, 2008, 10 (13) :2901-2904

[2] Cyclic nucleotide research - still expanding after half a century [J].

Beavo, JA ;

Brunton, LL .

NATURE REVIEWS MOLECULAR CELL BIOLOGY, 2002, 3 (09) :710-718

[3] Epac: a new cAMP target and new avenues in cAMP research [J].

Bos, JL .

NATURE REVIEWS MOLECULAR CELL BIOLOGY, 2003, 4 (09) :733-738

[4]

Cahiez G, 1998, SYNTHESIS-STUTTGART, P1199

[5] Ansellone A, a Sesterterpenoid Isolated from the Nudibranch Cadlina luteromarginata and the Sponge Phorbas sp., Activates the cAMP Signaling Pathway [J].

Daoust, Julie ;

Fontana, Angelo ;

Merchant, Catherine E. ;

de Voogd, Nicole J. ;

Patrick, Brian O. ;

Kieffer, Timothy J. ;

Andersen, Raymond J. .

ORGANIC LETTERS, 2010, 12 (14) :3208-3211

[6] Visualization of PKA activity in plasma membrane microdomains [J].

Depry, Charlene ;

Allen, Michael D. ;

Zhang, Jin .

MOLECULAR BIOSYSTEMS, 2011, 7 (01) :52-58

[7] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[8] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[9] The role of membrane microdomains in shaping β2-adrenergic receptor-mediated cAMP dynamics [J].

DiPilato, Lisa M. ;

Zhang, Jin .

MOLECULAR BIOSYSTEMS, 2009, 5 (08) :832-837

[10] Enantioselective Synthesis of a Diastereomer of Iriomoteolide-1a. What Is the Correct Structure of the Natural Product? [J].

Fang, Lijing ;

Yang, Jiong ;

Yang, Fei .

ORGANIC LETTERS, 2010, 12 (14) :3124-3127

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