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Synlett

Volumn , Issue 18, 2007, Pages 2891-2893

Concise total synthesis of (-)-muricatacin and (-)-iso-cladospolide B using chemoselective cross-metathesis

(4) Ferrié, Laurent a Reymond, Sébastien a Capdevielle, Patrice a Cossy, Janine a

a CNRS (France)

Author keywords

Chemoselectivity; Cross coupling; Dihydroxylations; Metathesis; Total synthesis

Indexed keywords

ACETOGENIN; CLADOSPOLIDE; MACROLIDE; MURICATACIN; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL REACTION; CHEMOSELECTIVITY; CROSS COUPLING REACTION; CYTOTOXICITY; DIHYDROXYLATION; RING CLOSING METATHESIS; SYNTHESIS;

EID: 36549032080 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-990958 Document Type: Article

Times cited : (38)

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- +].
- +].

41
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- Modified AD-mix: OsO4 (2 mol, DHQ)2PHAL for ADmix α (4 mol, or (DHQD)2PHAL for AD-mix γ (4 mol, MeSO2NH2 (1 equiv, K3Fe(CN)6 (3 equiv, K2CO3 3 equiv, t-BuOH-H2O, see ref. 8c
- 2O, see ref. 8c.

42
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- R (R,R) = 6.50 min].
- R (R,R) = 6.50 min].

43
- 36549079909
- Muricatacin (prepared in <1 mmol scale, mp 69-72°C (synthetic product3j mp 68-70°C, α]D20 -19.6 (c 1.0, CHCl3, isolated natural product5 [α]D20 -16.1; reported synthetic produce [α]D23 -19.5 (c 2.1, CHCl3, IR (neat, 3396, 3000-2800, 1727, 1470, 1176 cm-1. 1H NMR (400 MHz, CDCl3, δ, 4.41 (td, J, 7.5, 4.6 Hz, 1 H, 3.57 (m, 1 H, 2.62 (ddd, J, 17.8, 9.9, 5.0 Hz, 1 H, 2.54 (ddd, J, 17.8, 9.5, 9.0 Hz, 1 H, 2.30-2.20 (m, 1 H, 2.17-2.06 (m, 1 H, 1.88 (m, 1 H, OH, 1.60-1.18 (m, 22 H, 0.88 (t, J, 6.7 Hz, 3 H, 13C NMR (100 MHZ, CDCl3, δ, 177.1 (s, 82.9 (d, 73.7 (d, 33.0 (t, 31.9 (t, 29.6 (t, 29.6 (t, 29.6 (t, 29.5 (t, 29.5 (t, 29.5 (t, 29.3 (t, 28.9 (t, 25.4 (t, 24.1 (t, 22.7 (t, 14.1 (q, MS EI, m/z
- +: 307.2244; found: 307.2239.

44
- 36549052033
- iso-Cladospolide B (prepared in <1 mmol scale, α]D20 -61.6 (c 0.50, MeOH, isolated natural product4c [α]D28 -61.0 (c 16.6, MeOH, IR (neat, 3487, 3000-2800, 1745, 1462, 1329, 1165, 1097, 1042, 828 cm-1. 1HNMR (400 MHz, CDCl3, δ, 7.46 (dd, J, 5.8, 1.5 Hz, 1 H, 6.18 (dd, J, 5.8, 2.0 Hz, 1 H, 4.99 (dtapp, J, 4.5, 1.8 Hz, 1 H, 3.86-3.66 (m, 2 H, 2.21-1.81 (m, 2 H, OH, 1.66-1.26 (m, 10 H, 1.18 (d, J, 6.2 Hz, 3 H, 13C NMR (100 MHz, CDCl3, δ, 172.9 (s, 153.8 (d, 122.7 (d, 86.2 (d, 71.7 (d, 68.0 (d, 39.0 (t, 33.0 (t, 29.3 (t, 25.5 (t, 25.4 (t, 23.5 (q, ESI-HRMS ESI, m/z calcd for C12H 20O4, Na, 251.1248; found: 251.1253
- +: 251.1248; found: 251.1253.

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