Stereoselective Total Synthesis of Stagonolide C

被引：10

作者：

Yadav, Jhillu S. ^{[1
,2
]}

Reddy, Nimmakayala Mallikarjuna ^{[1
]}

Rao, N. Venkateswar ^{[1
]}

Rahman, Md Ataur ^{[1
]}

Prasad, Attaluri R. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India

[2] King Saud Univ, Riyadh 11451, Saudi Arabia

来源：

HELVETICA CHIMICA ACTA | 2012年 / 95卷 / 02期

关键词：

Stagonolide C; Prins cyclization; Alkene rearrangement; Ring-closing metathesis; REDUCTIVE CLEAVAGE SEQUENCE; PRINS CYCLIZATION; STAGONOSPORA-CIRSII; DIASTEREOSELECTIVE SYNTHESIS; POTENTIAL MYCOHERBICIDE; LEUCASCANDROLIDE-A; FORMAL SYNTHESIS; TETRAHYDROPYRANOLS; MODIOLIDE; CATALYSTS;

D O I：

10.1002/hlca.201100190

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent and efficient total synthesis of stagonolide C (1), a phytotoxic metabolite, was achieved (Schemes 2 and 3) The synthesis exploited the high configuration control in the Prins cyclization along with alkene rearrangement and ring-closing metathesis as key steps.

引用

页码：227 / 234

页数：8

共 50 条

[1] Stereoselective total synthesis of stagonolide-C
Venkatesham, Akkaladevi
Nagaiah, Kommu
TETRAHEDRON-ASYMMETRY, 2012, 23 (15-16) : 1186 - 1197
[2] Stereoselective Total Synthesis of Stagonolide C and Formal Total Synthesis of Modiolide A
Mohapatra, Debendra K.
Dash, Uttam
Naidu, P. Ramesh
Yadav, J. S.
SYNLETT, 2009, (13) : 2129 - 2132
[3] Stereoselective Total Synthesis of Stagonolide E
Rajaram, Singanaboina
Ramulu, Udugu
Aravind, Seema
Babu, Katragadda Suresh
HELVETICA CHIMICA ACTA, 2015, 98 (05) : 650 - 656
[4] Stereoselective total synthesis of stagonolide E
Sabitha, Gowravaram
Padmaja, P.
Reddy, P. Narayana
Jadav, Surender Singh
Yadav, J. S.
TETRAHEDRON LETTERS, 2010, 51 (47) : 6166 - 6168
[5] The Stereoselective Total Synthesis of (+)-Stagonolide B
Srihari, Pabbaraja
Kumaraswamy, Boyapelly
Somaiah, Ragam
Yadav, Jhillu S.
SYNTHESIS-STUTTGART, 2010, (06): : 1039 - 1045
[6] First stereoselective total synthesis of (-)-stagonolide A
Srihari, Pabbaraja
Kumaraswamy, Boyapelly
Rao, Gokada Maheswara
Yadav, Jhillu Singh
TETRAHEDRON-ASYMMETRY, 2010, 21 (01) : 106 - 111
[7] First stereoselective total synthesis of stagonolide G
Srihari, P.
Kumaraswamy, B.
Bhunia, Dinesh C.
Yadav, J. S.
TETRAHEDRON LETTERS, 2010, 51 (21) : 2903 - 2905
[8] A Stereoselective Aldol Approach for the Total Synthesis of Herbarumin I and Stagonolide A
Srihari, P.
Rao, G. Maheswara
Rao, R. Srinivasa
Yadav, J. S.
SYNTHESIS-STUTTGART, 2010, (14): : 2407 - 2412
[9] First stereoselective total synthesis and reconfirmation of absolute structure of nonenolide (-)-stagonolide D
Kumar, A. Sravanth
Praneeth, K.
Srihari, P.
Yadav, J. S.
TETRAHEDRON LETTERS, 2017, 58 (06) : 509 - 511
[10] Total synthesis of stagonolide B
Das, Tapas
Mahapatra, Tridib
Nanda, Samik
TETRAHEDRON LETTERS, 2012, 53 (09) : 1186 - 1189

← 1 2 3 4 5 →