Comments on Recent Achievements in Biomimetic Organic Synthesis

Angewandte Chemie - International Edition

Volumn 43, Issue 2, 2003, Pages 160-181

  De La Torre, María C ^a   Sierra, Miguel A ^b  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Biomimetic synthesis; Enzymes; Natural products; Organic synthesis

Indexed keywords

BIOSYNTHESIS; CATALYSIS; ENZYME KINETICS;

BIOGENESIS;

BIOMIMETIC MATERIALS;

ENZYME; ISOPRENOID; NATURAL PRODUCT; POLYETHER;

ACHIEVEMENT; BIOGENESIS; BIOMIMETICS; CATALYSIS; CYCLIZATION; DIELS ALDER REACTION; ORGANIC CHEMISTRY; OXIDATION; REVIEW; SYNTHESIS;

MOLECULAR MIMICRY; ORGANIC CHEMICALS;

EID: 0345862320     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200200545     Document Type: Review

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154. a) E. Wenkert, B. Wickberg, J. Am. Chem. Soc. 1965, 87, 1580-1589;
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160. R. Robinson, S. Sugasawa, J. Chem. Soc. 1933, 280-281. One reviewer provided us with an interesting history of the genesis of the oxidative work on biomimetic synthesis and the biogenesis of these alkaloids: In 1925, the oxidative dimerization of p-cresol was described, but the structure of the resulting product was assigned incorrectly (R. Pummerer, H. Puttfarcken, P. Schopflocher, Ber. Dtsch. Chem. Ges. B 1925, 58, 1808-1820). Robinson's early views on the biogenesis of morphine and its congeners were based on the flawed structure of that ketone. It was Barton who formulated the correct structure and elaborated a set of simple rules for oxidative phenolic radical coupling (D. H. R. Barton, T. Cohen, Festschrift Prof. A. Stoll zum siebzigsten Geburtstag, Birkhäuser, Basel, 1957).
161. R. Robinson, S. Sugasawa, J. Chem. Soc. 1933, 280-281. One reviewer provided us with an interesting history of the genesis of the oxidative work on biomimetic synthesis and the biogenesis of these alkaloids: In 1925, the oxidative dimerization of p-cresol was described, but the structure of the resulting product was assigned incorrectly (R. Pummerer, H. Puttfarcken, P. Schopflocher, Ber. Dtsch. Chem. Ges. B 1925, 58, 1808-1820). Robinson's early views on the biogenesis of morphine and its congeners were based on the flawed structure of that ketone. It was Barton who formulated the correct structure and elaborated a set of simple rules for oxidative phenolic radical coupling (D. H. R. Barton, T. Cohen, Festschrift Prof. A. Stoll zum siebzigsten Geburtstag, Birkhäuser, Basel, 1957).
162. R. Robinson, S. Sugasawa, J. Chem. Soc. 1933, 280-281. One reviewer provided us with an interesting history of the genesis of the oxidative work on biomimetic synthesis and the biogenesis of these alkaloids: In 1925, the oxidative dimerization of p-cresol was described, but the structure of the resulting product was assigned incorrectly (R. Pummerer, H. Puttfarcken, P. Schopflocher, Ber. Dtsch. Chem. Ges. B 1925, 58, 1808-1820). Robinson's early views on the biogenesis of morphine and its congeners were based on the flawed structure of that ketone. It was Barton who formulated the correct structure and elaborated a set of simple rules for oxidative phenolic radical coupling (D. H. R. Barton, T. Cohen, Festschrift Prof. A. Stoll zum siebzigsten Geburtstag, Birkhäuser, Basel, 1957).
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179. a) T. Momose, T. Nakamura, K.-I. Kanai, Heterocycles 1977, 6, 277-280;
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182. for the biomimetic synthesis of galanthamine, see: d) D. H. R. Barton, G. W. Kirby, J. Chem. Soc. 1962, 806-817.
183. M. Node, S. Kodama, Y. Hamashima, T. Baba, N. Hamamichi, K. Nishide, Angew. Chem. 2001, 113, 3150-3152; Angew. Chem. Int. Ed. 2001, 40, 3060-3062.
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186. For the earlier development of nonmetallic oxidative agents to effect the biomimetic oxidative phenolic coupling (during the synthesis of (-)-codeine), with a subsequent improvement in yield, see: J. D. White, G. Caravatti, T. B. Kline, E. Edstrom, Tetrahedron 1983, 39, 2393-2398.
187. For an excellent review on the chemistry of the ellagitannins, see: S. Quideau, K. S. Feldman, Chem. Rev. 1996, 96, 475-503.
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192. K. S. Feldman, A. Sambandam, J. Org. Chem. 1995, 60, 8171-8178.
193. There is an additional interesting point related to the biosynthesis of the ellagitannins: In the oxidative aryl coupling hypothesis, the ellagitannins are derived from a fully galloylated glucose precursor. Therefore, those ellagitannins with unacylated hydroxy groups on the glucose frame would result from the hydrolysis of fully galloylated monomers or oligomers within the plant cell, with concomitant release of either gallic acid (155) or ellagic acid (156). According to Quideau and Feldman, (reference [72], p. 481): "it is, however, possible that hydrolysis may also occur post mortem. This unfortunate ambiguity raises concerns when identifying isolates as a bona fide natural products".
194. a) D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2704;
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200. For two excellent reviews on the chemistry and biology of vancomycin antibiotics, see: a) D. H. Williams, B. Bardsley, Angew. Chem. 1999, 111, 1264-1286; Angew. Chem. Int. Ed. 1999, 38, 1172-1193;
201. K. C. Nicolaou, C. N. C. Boddy, S. Bräse, N. Winssinger, Angew. Chem. 1999, 111, 2230-2287; Angew. Chem. Int. Ed. 1999, 38, 2096-2152.
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203. a) D. Bischoff, S. Pelzer, B. Bister, G. J. Nicholson, S. Stockert, M. Schirle, W. Wohlleben, G. Jung, R. D. Süssmuth, Angew. Chem. 2001, 113, 4824-4827; Angew. Chem. Int. Ed. 2001, 40, 4688-4691;
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209. For the synthesis of the orientincin C aglycon, see: a) D. A. Evans, C. J. Dinsmore, A. M. Ratz, D. A. Evrard, J. C. Borrow, J. Am. Chem. Soc. 1997, 119, 3417-3418;
210. b) D. A. Evans, J. C. Barrow, P. S. Watson, A. M. Ratz, C. J. Dinsmore, D. A. Evrard, K. M. DeVries, J. A. Ellman, S. D. Rychnovsky, J. Lacour, J. Am. Chem. Soc. 1997, 119, 3419-3420.
211. D. A. Evans, C. J. Dinsmore, Tetrahedron Lett. 1993, 34, 6029-6032.
212. A. B. Smith III, C. M. Adams, S. A. Kozmin, D. V. Paone, J. Am. Chem. Soc. 2001, 123, 5925-5937.
213. a) K. C. Nicolaou, W. Qian, F. Bernal, N. Uesaka, P. M. Pihko, J. Hinrichs, Angew. Chem. 2001, 113, 4192-4195; Angew. Chem. Int. Ed. 2001, 40, 4068-4071;
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216. b) K. C. Nicolaou, P. M. Pihko, N. Diedrichs, N. Zou, F. Bernal, Angew. Chem. 2001, 113, 1302-1305; Angew. Chem. Int. Ed. 2001, 40, 1262-1265; Corrigendum: K. C. Nicolaou, P.M. Pihko, N. Diedrichs, N. Zou, F. Bernal, Angew. Chem. 2001, 113, 1621; Angew. Chem. Int. Ed. 2001, 40, 1573
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219. a) B. S. Moore, J.-L. Chen, G. M. L. Patterson, R. E. Moore, L. S. Brinen, Y. Kato, J. Clardy, J. Am. Chem. Soc. 1990, 112, 4061-4063;
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221. Evidently, there is a different point of view. Based on a definition of a natural product as a substance that has no known role in the internal economy of the producing organism, Williams et al. "...propose that all such structures serve the producing organisms by improving their survival fitness. We argue that this conclusion is necessitated by the fact that natural products are normally complex structures, whose biosynthesis is programmed by many kilobases of DNA. If it were otherwise, the pressures of Darwinian natural selection would have precluded the expenditure of so much metabolic energy in their construction and the development of such complexity." (D. H. Williams, M. J. Stone, P. R. Hauck, S. K. Rahman, J. Nat. Prod. 1989, 52, 1189-1208).
222. See, for example, the excellent article about whether or not enzymes obey Baldwin's rules: J. A. Piccirilli, Chem. Biol. 1999, 6, R59-R64.
223. For selected reviews, see: a) Y. Murakami, J. Kikuchi, Y. Hisaeda, O. Hayashida, Chem. Rev. 1996, 96, 721-758;
224. b) R. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997-2012;
225. c) W. B. Motherwell, M. J. Bingham, Y. Six, Tetrahedron 2001, 57, 4663-4686.