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Synlett 2010(17): 2636-2638  
DOI: 10.1055/s-0030-1258583
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Total Synthesis of (+)-Sapinofuranone B

J. S. Yadav*, J. Shyam Sunder Reddy, S. S. Mandal, P. Srihari
Organic Division - I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160387; e-Mail: yadavpub@iict.res.in;
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Publication History

Received 13 August 2010
Publication Date:
23 September 2010 (online)

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Abstract

A stereoselective total synthesis of sapinofuranone B is described starting from commercially available l-(+)-diethyl tartrate using a ring-opening reaction, a Mitsunobu inversion, and a Sonogashira coupling as the key steps.

Key words

ring-opening - Mitsunobu - acetonide - Sonogashira - γ-lactones

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15

Spectroscopic data for selected compounds. Compound 3: [α] d ²8 +20.1 (c 0.53, CHCl3) {Lit.² +19.0 (c 0.77, CHCl3)}. ¹H NMR (500 MHz, CDCl3): δ = 1.80 (dd, J = 6.6 Hz, 3 H), 1.94-2.37 (m, 2 H), 2.45-2.69 (m, 2 H), 4.46 (dd, J = 6.8, 12.8 Hz, 1 H), 4.57 (dd, J = 5.8, 8.8 Hz, 1 H), 5.30 (t, J = 10.0 Hz, 1 H), 5.85 (qd, J = 6.9, 13.9 Hz, 1 H), 6.19 (t, J = 11.0 Hz, 1 H), 6.28-6.42 (m, 1 H). ¹³C NMR (75 MHz, CDCl3): δ = 18.4, 23.7, 28.4, 70.1, 82.8, 123.9, 126.0, 133.8, 133.9, 177.0. IR (neat): 3383, 2924, 2854, 1767, 1460, 1184, 1039 cm-¹. MS (LC-MS): m/z = 205 [M + Na]+. HRMS:
m/z calcd for C10H14NaO3: 205.0849; found: 205.0840. Compound 7: [α] d ²5 +18.7 (c 1.2, CHCl3). ¹H NMR (300 MHz, CDCl3): δ = 1.54-1.84 (m, 4 H), 2.39 (d, J = 2.2 Hz, 1 H), 3.33 (s, 3 H), 3.46-3.60 (m, 5 H), 4.10-4.27 (m, 2 H), 4.56 (s, 2 H), 4.71 (Abq, J = 7.2 Hz, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 25.8, 28.5, 55.1, 56.0, 65.1, 67.3, 74.1, 81.7, 84.6, 96.3, 97.8. IR (neat): 3418, 3279, 2937, 2150, 1646, 1447, 1381, 1150, 1106, 1037, 917 cm-¹. MS (LC-MS): m/z = 255 [M + Na]+. HRMS: m/z calcd for C11H20NaO5: 255.1208; found: 255.1203. Compound 11: [α] d ²5 +8.0 (c 1.0, CHCl3). ¹H NMR (200 MHz, CDCl3): δ = 0.10 (s, 6 H), 0.91 (s, 9 H), 1.35 (s, 3 H), 1.37 (s, 3 H), 2.14-2.23 (m, 1 H), 2.40-2.49 (m, 1 H), 2.90 (br s, 1 H, OH), 3.59-3.70 (m, 3 H), 3.81-3.90 (m, 2 H), 5.07-5.16 (m, 2 H), 5.82-5.96 (m, 1 H). ¹³C NMR (75 MHz, CDCl3): δ = -5.5, 18.3, 25.8, 26.8, 26.9, 37.8, 64.2, 71.5, 79.5, 81.6, 108.8, 117.5, 134.5. IR (neat): 3447, 2932, 1617, 1379, 1254, 1082, 837, 774 cm-¹. MS (LC-MS): m/z = 339 [M + Na]+. HRMS: m/z calcd for C16H32SiNaO4: 339.1967; found: 339.1970