Synthetic Studies on Ecteinascidin 743 (Et 743): Asymmetric Synthesis of a Highly Oxygenated Tetrahydroisoquinoline via a Key Phenolic Mannich Reaction

Xiaochuan Chen; Jinchun Chen; Jieping Zhu

doi:10.1055/s-2006-950343

SPECIALTOPIC

Synthetic Studies on Ecteinascidin 743 (Et 743): Asymmetric Synthesis of a Highly Oxygenated Tetrahydroisoquinoline via a Key Phenolic Mannich Reaction

Xiaochuan Chen, Jinchun Chen, Jieping Zhu*
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France
Fax: +33(1)69077247; e-Mail: zhu@icsn.cnrs-gif.fr;

Abstract

All articles of this category

Abstract

The Mannich reaction between a phenol and a chiral oxazinone is used as a key step in a concise synthesis of a highly functionalized, orthogonally protected amino triol. The utility of such an approach is illustrated by a concise synthesis of a highly oxygenated tetrahydroisoquinoline, a key structural unit of ecteinascidin 743 (Et 743) and related natural products.

Key words

ecteinascidin 743 (Et 743) - Mannich reaction - Pomerantz-Fritsch cyclization - oxazinone - tetrahydroisoquinoline

Full Text

References

<A NAME="RC05206SS-1A">1a</A> Rinehart KL. Holt TG. Fregeau NL. Stroh JG. Shield LS. Seigler DS. J. Nat. Prod. 1990, 53: 771

<A NAME="RC05206SS-1B">1b</A> Wright AE. Forleo DA. Gunawardana GP. Gunasekera SP. Koehn FE. McConnell OJ. J. Org. Chem. 1990, 55: 4508

<A NAME="RC05206SS-1C">1c</A> Suwanborirux K. Charupant K. Amnuoypol S. Pummangura S. Kubo A. Saito N. J. Nat. Prod. 2002, 65: 935

<A NAME="RC05206SS-2">2</A> Rinehart KL. Med. Drug. Rev. 2000, 1

<A NAME="RC05206SS-3">3</A> Scott JD. Williams RM. Chem. Rev. 2002, 102: 1669

<A NAME="RC05206SS-4A">4a</A> Corey EJ. Gin DY. Kania RS. J. Am. Chem. Soc. 1996, 118: 9202

<A NAME="RC05206SS-4B">4b</A> Corey EJ. Gin DY. Tetrahedron Lett. 1996, 37: 7163

<A NAME="RC05206SS-5A">5a</A> Endo A. Yanagisawa A. Abe M. Tohma S. Kan T. Fukuyama T. J. Am. Chem. Soc. 2002, 124: 2545

<A NAME="RC05206SS-5B">5b</A> Endo A. Kann T. Fukuyama T. Synlett 1999, 1103

<A NAME="RC05206SS-6">6</A> Chen J. Chen X. Bois-Choussy M. Zhu J. J. Am. Chem. Soc. 2006, 128: 87

<A NAME="RC05206SS-7A">7a</A> Zheng S. Chan C. Furuuchi T. Wright BJD. Zhou B. Guo J. Danishefsky SJ. Angew. Chem. Int. Ed. 2006, 45: 1754

<A NAME="RC05206SS-7B">7b</A> Chan C. Zheng S. Zhou B. Guo J. Heid RH. Wright BJD. Danishefsky SJ. Angew. Chem. Int. Ed. 2006, 45: 1749

<A NAME="RC05206SS-8A">8a</A> Cuevas C. Pérez M. Martin MJ. Chicharro JL. Fernandez-Rivas C. Flores M. Francesch A. Gallego P. Zarzuelo M. De La Calle F. Garcia J. Polanco C. Rodriguez I. Manzanares I. Org. Lett. 2000, 2: 2545

<A NAME="RC05206SS-8B">8b</A> Menchaca R. Martínez V. Rodríguez A. Rodríguez N. Flores M. Gallego P. Manzanares I. Cuevas C. J. Org. Chem. 2003, 68: 8859

<A NAME="RC05206SS-9A">9a</A> Saito N. Kamayachi H. Tachi M. Kubo A. Heterocycles 1999, 51: 9

<A NAME="RC05206SS-9B">9b</A> Saito N. Tachi M. Seki R. Kamayachi H. Kubo A. Chem. Pharm. Bull. 2000, 48: 1549

<A NAME="RC05206SS-10A">10a</A> Herberich B. Kinugawa M. Vazquez A. Williams RM. Tetrahedron Lett. 2001, 42: 543

<A NAME="RC05206SS-10B">10b</A> Jin W. Williams RM. Tetrahedron Lett. 2003, 44: 4635

<A NAME="RC05206SS-10C">10c</A> Jin W. Metobo S. Williams RM. Org. Lett. 2003, 5: 2095

<A NAME="RC05206SS-11">11</A> Magnus P. Matthews KS. Lynch V. Org. Lett. 2003, 5: 2181

<A NAME="RC05206SS-12">12</A> Tang Y.-F. Liu Z.-Z. Chen S.-Z. Tetrahedron Lett. 2003, 44: 7091

<A NAME="RC05206SS-13">13</A> Aubry S. Pellet-Rostaing S. Fenet B. Lemaire M. Tetrahedron Lett. 2006, 47: 1319

<A NAME="RC05206SS-14">14</A> Ceballos PA. Péres M. Cuevas C. Francesch A. Manzanares I. Echavarren AM. Eur. J. Org. Chem. 2006, 1926

<A NAME="RC05206SS-15A">15a</A> De Paolis M. Chiaroni A. Zhu J. Chem. Commun. 2003, 2896

<A NAME="RC05206SS-15B">15b</A> Chen X. Chen J. De Paolis M. Zhu J. J. Org. Chem. 2005, 70: 4397

<A NAME="RC05206SS-15C">15c</A> De Paolis M. Chen X. Zhu J. Synlett 2004, 729

<A NAME="RC05206SS-16">16</A> Fishlock D. Williams RM. Org. Lett. 2006, 8: 3299

Chiral oxazinone has been used as an efficient glycine template for the synthesis of enantiomerically pure amino acids. For selected examples, see:

<A NAME="RC05206SS-17A">17a</A> Vigneron JP. Kagan H. Horeau A. Tetrahedron Lett. 1968, 5681

<A NAME="RC05206SS-17B">17b</A> Cox GC. Harwood LM. Tetrahedron: Asymmetry 1994, 5: 1669

<A NAME="RC05206SS-17C">17c</A> Harwood LM. Vines KJ. Drew MGB. Synlett 1996, 1051

<A NAME="RC05206SS-17D">17d</A> Harwood LM. Tyler SNG. Anslow AS. MacGilp ID. Drew MGB. Tetrahedron: Asymmetry 1997, 8: 4007

For radical addition, see:

<A NAME="RC05206SS-17E">17e</A> Bertrand MP. Coantic S. Feray L. Nouguier R. Perfetti P. Tetrahedron 2000, 56: 3951

<A NAME="RC05206SS-17F">17f</A> Ueda M. Miyabe H. Teramachi M. Miyata O. Naito T. Chem. Commun. 2003, 426

<A NAME="RC05206SS-18A">18a</A> Tohma S. Endo A. Kan T. Fukuyama T. Synlett 2001, 1179

<A NAME="RC05206SS-18B">18b</A> Tohma S. Rikimaru K. Endo A. Shimamoto K. Kan T. Fukuyama T. Synthesis 2004, 909 ; and reference 5

<A NAME="RC05206SS-19A">19a</A> Lei F. Chen Y.-J. Sui Y. Liu L. Wang D. Synlett 2003, 1160

<A NAME="RC05206SS-19B">19b</A> Chen Y.-J. Lei F. Liu L. Wang D. Tetrahedron 2004, 59: 7609

<A NAME="RC05206SS-20">20</A> Williams RM. Hendrix JA. Chem. Rev. 1992, 92: 889

<A NAME="RC05206SS-21">21</A> From (R)-serine: a) SOCl₂, MeOH; b) TBDMSCl, DMF, imidazole; c) NaBH₄, LiCl, THF, MeOH; overall yield: 64%

<A NAME="RC05206SS-22">22</A> Dellaria JF. Santarsiero BD. J. Org. Chem. 1989, 54: 3916

<A NAME="RC05206SS-23">23</A> For stereoselective and stereodivergent Mannich reaction, see: Rondot C. Zhu J. Org. Lett. 2005, 7: 1641 ; and references cited therein

<A NAME="RC05206SS-24">24</A> Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508

For recent reviews on microwave-assisted organic synthesis, see:

<A NAME="RC05206SS-25A">25a</A> Larhed M. Moberg C. Hallberg A. Acc. Chem. Res. 2002, 35: 717

<A NAME="RC05206SS-25B">25b</A> Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250

For a monograph, see:

<A NAME="RC05206SS-25C">25c</A> Microwaves in Organic Synthesis Loupy A. Wiley-VCH; Weinheim: 2002.

<A NAME="RC05206SS-26">26</A> Jourdant A. Zhu J. Tetrahedron Lett. 2001, 42: 3431

<A NAME="RC05206SS-27">27</A> Stevens RV. Acc. Chem. Res. 1984, 17: 289

<A NAME="RC05206SS-28A">28a</A> Zhou B. Guo J. Danishefsky SJ. Tetrahedron Lett. 2000, 41: 2043

<A NAME="RC05206SS-28B">28b</A> Zhou B. Guo J. Danishefsky SJ. Org. Lett. 2002, 4: 43