Stereoselective Total Synthesis of iso-Cladospolide B

P. Srihari; E. Vijaya Bhasker; S. J. Harshavardhan; J. S. Yadav

doi:10.1055/s-2006-950317

PAPER

Stereoselective Total Synthesis of iso-Cladospolide B

P. Srihari*, E. Vijaya Bhasker, S. J. Harshavardhan, J. S. Yadav
Organic Division - I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: srihari@iict.res.in;

Abstract

All articles of this category

Abstract

A simple and efficient stereoselective total synthesis of iso-cladospolide B and a formal total synthesis of cladospolide B, using Jacobsen’s hydrolytic kinetic resolution, is described.

Key words

phytotoxic - Wadsworth-Emmons - oxidation - kinetic resolution - Mitsunobu

Full Text

References

<A NAME="RZ15106SS-1">1</A> Biabani MAF. Laatsch H. J. Prakt. Chem. 1998, 340: 589

<A NAME="RZ15106SS-2A">2a</A> Cameron JS. Abbanat D. Bernan VS. Maiese WM. Greenstein M. Jompa J. Tahir A. Ireland CM. J. Nat. Prod. 2000, 63: 142

<A NAME="RZ15106SS-2B">2b</A> Brauers G. Edrada RA. Ebel R. Proksch P. Wray V. Berg A. Grage U. Schachtele C. Totzke F. Finkezneller G. Marme D. Kraus J. Munchbach M. Michel M. Bringmann G. Schaumann K. J. Nat. Prod. 2000, 63: 739

<A NAME="RZ15106SS-2C">2c</A> Gestner S. Cohen N. Ilan M. Yarden O. Carmeli S. J. Nat. Prod. 2005, 68: 1350

<A NAME="RZ15106SS-3">3</A> Fuji Y. Fukuda A. Hamasaki T. Ichimoto I. Nakajima H. Phytochemistry 1995, 40: 1443

<A NAME="RZ15106SS-4A">4a</A> Pandey SK. Kumar P. Tetrahedron Lett. 2005, 46: 6625

<A NAME="RZ15106SS-4B">4b</A> Franck X. Vaz Araujo ME. Jullian JC. Hocquemiller R. Figadere B. Tetrahedron Lett. 2001, 42: 2801

<A NAME="RZ15106SS-4C">4c</A> Austin KAB. Banwell MG. Loong DTJ. Rae D. Willis AC. Org. Biomol. Chem. 2005, 3: 1081

<A NAME="RZ15106SS-5A">5a</A> Yadav JS. Vishweshwar RK. Sridhar RM. Prasad AR. Tetrahedron Lett. 2006, 47: 4393

<A NAME="RZ15106SS-5B">5b</A> Yadav JS. Prathap I. Padmaja TB. Tetrahedron Lett. 2006, 47: 3773

<A NAME="RZ15106SS-5C">5c</A> Yadav JS. Krishnam Raju A. Purushotham RP. Rajaiah G. Tetrahedron: Asymmetry 2005, 16: 3283

<A NAME="RZ15106SS-5D">5d</A> Sabitha G. Swapna R. Satheesh BR. Yadav JS. Tetrahedron Lett. 2005, 46: 6145

<A NAME="RZ15106SS-5E">5e</A> Yadav JS. Sridhar Reddy M. Prasad AR. Tetrahedron Lett. 2005, 46: 2133

<A NAME="RZ15106SS-5F">5f</A> Sabitha G. Rajkumar M. Shashi Kumar RM. Yadav JS. Ramakrishna KVS. Kunwar AC. Tetrahedron Lett. 2005, 46: 1659

<A NAME="RZ15106SS-5G">5g</A> Sudhakar K. Sabitha G. Mallikarjuna RN. Rajkumar M. Yadav JS. Tetrahedron Lett. 2005, 46: 6567

<A NAME="RZ15106SS-5H">5h</A> Yadav JS. Bhaskar RK. Sabitha G. Tetrahedron Lett. 2004, 45, 6475

<A NAME="RZ15106SS-5I">5i</A> Yadav JS. Srihari P. Tetrahedron: Asymmetry 2004, 15: 81

<A NAME="RZ15106SS-6A">6a</A> Tokunaga M. Larrow JF. Kakiuchim F. Jacobsen EN. Science 1997, 277: 936

<A NAME="RZ15106SS-6B">6b</A> For earlier publications using Salen complexes from our group, see ref. 5i and: Yadav JS. Bandyopadhyay A. Kunwar AC. Tetrahedron Lett. 2001, 43: 4907

<A NAME="RZ15106SS-7">7</A> Mitsunobu O. Synthesis 1981, 1

<A NAME="RZ15106SS-8A">8a</A> Julia M. Paris JM. Tetrahedron Lett. 1973, 14: 4833

Other bases were employed without success.

<A NAME="RZ15106SS-9">9</A> Garegg J. Samuelsson B. J. Chem. Soc., Perkin Trans. 1 1980, 2866

<A NAME="RZ15106SS-10A">10a</A> Hungebuhler E. Seebach D. Helv. Chim. Acta. 1981, 64: 687

<A NAME="RZ15106SS-10B">10b</A> Mukayama T. Suzuki K. Yamada T. Chem. Lett. 1982, 929

The physical and spectroscopic data were in full agreement with the literature (ref. 4b).

<A NAME="RZ15106SS-12">12</A> Inanaga J. Hirata K. Sacki H. Katsuki T. Yamaguchi M. Bull. Chem. Soc. Jpn. 1979, 52: 1989