Enantiomeric Synthesis of the SPIKET-P Enantiomers

Anubha Sharma; Prema Iyer; Sunita Gamre; Subrata Chattopadhyay

doi:10.1055/s-2004-822342

PAPER

Enantiomeric Synthesis of the SPIKET-P Enantiomers

Anubha Sharma, Prema Iyer, Sunita Gamre, Subrata Chattopadhyay*
Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai - 400 085, India
Fax: +91(22)5505151; e-Mail: schatt@apsara.barc.ernet.in;

Abstract

All articles of this category

Abstract

A convenient synthesis of the antipodes of the title compound has been developed starting from (R)-1,2,5,6-dicyclohexylidene mannitol. Some of the key features of the syntheses were simple reaction protocols, and stereoselective inversion of chiral 1,2-diol moiety via neighbouring group assisted acetylation.

Keywords

cytotoxic - (R)-1,2,5,6-dicyclohexylidene mannitol - enantiomeric synthesis

Full Text

References

<A NAME="RZ02504SS-1">1</A> Hyams JS. Lloyd CW. Microtubules Wiley-Liss; New York: 1994.

<A NAME="RZ02504SS-2">2</A> Kozeeski F. Arnal I. Wade RH. Curr. Biol. 1998, 8: 191

<A NAME="RZ02504SS-3">3</A> Pettit GR. Cichacz ZA. Gao F. Herald CL. Boyd MR. J. Org. Chem. 1993, 58: 1302

<A NAME="RZ02504SS-4A">4a</A> Bai R. Cichacz ZA. Herald CL. Pettit GR. Hamel E. Mol. Pharmacol. 1993, 44: 757

<A NAME="RZ02504SS-4B">4b</A> Bai R. Taylor GF. Cichacz ZA. Herald CL. Kepler JA. Pettit GR. Hamel E. Biochemistry 1995, 34: 9714

<A NAME="RZ02504SS-5">5</A> Huang H. Mao C. Jan S.-T. Uckun FM. Tetrahedron Lett. 2000, 41: 1699

<A NAME="RZ02504SS-6">6</A> Uckun FM. Mao C. Vassilev AO. Huang H. Jan S.-T. Bioorg. Med. Chem. Lett. 2000, 10: 541

<A NAME="RZ02504SS-7">7</A> Fusetani N. Shinoda K. Matsunaga S. J. Am. Chem. Soc. 1993, 115: 3977

<A NAME="RZ02504SS-8">8</A> Perron F. Albizati KF. Chem. Rev. 1989, 89: 1617

<A NAME="RZ02504SS-9A">9a</A> Sauret S. Cuer A. Gourcy J.-G. Jeminet G. Tetrahedron: Asymmetry 1995, 6: 1995

<A NAME="RZ02504SS-9B">9b</A> Crimmins MT. Rafferty SW. Tetrahedron Lett. 1996, 37: 5649

<A NAME="RZ02504SS-10">10</A> Sharma A. Chattopadhyay S. Tetrahedron: Asymmetry 1999, 10: 883

<A NAME="RZ02504SS-11A">11a</A> Villieras J. Rambund M. Synthesis 1986, 300

<A NAME="RZ02504SS-11B">11b</A> Takano S. Kurotaki A. Takahashi M. Ogasawara K. Synthesis 1986, 403

<A NAME="RZ02504SS-12">12</A> Lipshutz BH. Garcia E. Tetrahedron Lett. 1990, 31: 7261

<A NAME="RZ02504SS-13">13</A> Hungerbühler E. Naef R. Wasmuth D. Seebach D. Helv. Chim. Acta 1980, 63: 1960

<A NAME="RZ02504SS-14">14</A> Sauret S. Cuer A. Gourcy J.-G. Jeminet G. Tetrahedron 1993, 49: 2621

<A NAME="RZ02504SS-15">15</A> Chattopadhyay S. Mamdapur VR. Chadha MS. Bull. Chim. Soc. Fr. 1990, 127: 108

<A NAME="RZ02504SS-16">16</A> Yang W.-Q. Kitahara T. Tetrahedron 2000, 56: 1451