Use of Chiral Sulfoxide in the Asymmetric Synthesis of (+)-Virol C

Hélio A.  Stefani; Paulo H.  Menezes; Iguatemi M.  Costa; Diogo O.  Silva; Nicola  Petragnani

doi:10.1055/s-2002-32973

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2002(8): 1335-1337
DOI: 10.1055/s-2002-32973

LETTER

Use of Chiral Sulfoxide in the Asymmetric Synthesis of (+)-Virol C

Hélio A. Stefani*^a, Paulo H. Menezes^b, Iguatemi M. Costa^a, Diogo O. Silva^a, Nicola Petragnani^c
^a Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil
Fax: +55(11)38154418; e-Mail: hstefani@usp.br;
^b Depto. de Química Fundamental, Universidade Federal de Pernambuco, Recife, PE, Brazil
^c Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil

Further Information

Publication History

Received 24 April 2002
Publication Date:
25 July 2002 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

The total synthesis of virol C 1 was accomplished using a diastereoselective carbonyl reduction induced by a chiral sulfoxide, a Pummerer rearrangement to give the corresponding aldehyde fragment, and coupling reactions using Wittig and Cadiot-Chodkiewicz protocols.

Key words

natural products - chiral sulfoxides - total synthesis - copper-coupling - Pummerer reaction

References

1 Jacobson CA. J. Am. Chem. Soc. 1915, 37: 916

Crossref Google Scholar
2a Anet ERLJ. Silk MH. Trippett S. Chem. Ind. (London) 1952, 757

Google Scholar
2b Anet EFLJ. Silk MH. Trippet S. J. Chem. Soc. 1953, 309

Google Scholar
3 Uwai K. Oshima Y. Sugihara T. Ohta T. Tetrahedron 1999, 55: 9469

Crossref Google Scholar
4 Ohta T. Uwai K. Kikuchi R. Nozoe S. Oshima Y. Sasaki K. Yoshizaki R. Tetrahedron 1999, 55: 12087

Crossref Google Scholar
5 Stefani HA. Costa IM. Zeni G. Tetrahedron Lett. 1999, 40: 9215

Crossref Google Scholar
6 Solladié G. Almario A. Tetrahedron Lett. 1994, 35: 1937

Crossref Google Scholar
7 Solladié G. Greck C. Demailly G. Solladié-Cavallo A. Tetrahedron Lett. 1982, 23: 5047

Crossref Google Scholar
8 Corey EJ. Venkteswarlu A. J. Am. Chem. Soc. 1972, 94: 6190

Crossref Google Scholar
9a Pummerer R. Chem. Ber. 1909, 42: 2282

Article in Thieme Connect Google Scholar
9b Sugihara H. Tanikaga R. Kaji A. Synthesis 1978, 881

Article in Thieme Connect Google Scholar
10 De Lucchi O. Miotti U. Modena G. Org. React. 1991, 40: 157

Google Scholar
11 English J. Griswold PH. J. Am. Chem. Soc. 1945, 67: 2039

Crossref Google Scholar
12 Belyaev NN. Stadnichuk MD. Petrov AA. Belyaev AN. J. Gen. Chem. (USSR) 1972, 42: 710

Google Scholar
13 Nishikawa T. Shibuya S. Hosokawa S. Isobe M. Synlett 1994, 485

Article in Thieme Connect Google Scholar
14 Corey EJ. Ruden RA. Tetrahedron Lett. 1973, 17: 1495

Google Scholar
15 Alami M. Ferri F. Tetrahedron Lett. 1996, 37: 2763

Crossref Google Scholar

16

Compound 7. [α]_D +192º, (c 0.97, CHCl₃). ¹H NMR (CDCl₃) δ: 7.52 (d, J = 8 Hz, 2 H, Ho); 7.35 (d, J = 8 Hz, 2 H, Hm); 4.20-4.12 (m, 1 H, CHOH); 3.02 (dd, J ₁ = 13.5 Hz, J ₂ = 10 Hz, 1 H); 2.67 (dd, J ₁ = 3.5 Hz, J ₂ = 10 Hz, 1 H); 2.42 (s, 3 H); 1.82 (br. 1 H, OH); 1.73-1.24 (m, 12 H), 0.86 (t, J = 6.5 Hz, 3 H).¹³C NMR (CDCl₃) δ:141.53 (1 C, p); 139.58 (1 C, ipso);130.07 (2 C, m); 124.01 (2 C, o); 66.64 (1 C, CHOH); 61.50; 37.04; 31.75; 29.34; 29.15; 25.14; 22.61; 21.40; 14.07. IR (KBr) 3367; 2954; 2921; 2852; 1087; 1005; 812 cm^-1. MS m/z (%): 282 (M⁺, 2.10), 265(30); 140(100); 92(32); 69(17); 55(15); 43(18). Calcd for C₁₆H₂₆O₂S; C, 68.04; H, 9.28. Found: C, 68.12; H, 9.20. Compound 1. [α]_D +6.2, (c = 0.80, MeOH) (lit.⁴ [α]_D +6.4, (c = 0.82, MeOH).¹H NMR (CDCl₃) δ: 6.27 (dd, J ₁ = 16 Hz, J ₂ = 6 Hz, 1 H); 5.73 (d, J = 16 Hz, 1 H); 4.15 (br, 1 H); 3.74 (t, J ₁ = 6 Hz, 2 H); 2.47 (t, J = 6 Hz, 2 H); 1.80 (quint, J = 6 Hz, 2 H); 1.52-1.48 (m, 2 H); 1.47-1.26 (m, 10 H); 0.88 (t, J = 6 Hz, 3 H). ¹³C NMR (CDCl₃) δ: 149.0; 108.6; 83.5; 74.7; 73.3; 72.1; 65.5; 61.4; 36.9; 31.7; 30.8; 29.3; 29.1; 25.1; 22.5; 16.0; 13.9. IR (CHCl₃): 3608, 3439, 3013, 2932, 2859, 2236, 2140 cm^-1. MS m/z (%): 262 (M⁺) 231; 217; 191; 177; 163; 149; 135; 127; 57. Calcd for C₁₇H₂₆O₂; C, 77.81; H, 9.99. Found: C, 77.41; H, 10.10.