Further Extensions of the Kinetic Enolate Method for Terpenoid Syntheses

Author:

Ferriño S. A.,Maldonado L. A.

Publisher

Informa UK Limited

Subject

Organic Chemistry

Reference8 articles.

1. Synthesis of Terpenoids. IV. The Use of Kinetic Enolates of some Methyl Ketones For Terpenoid Syntheses

2. Aldehyde1was prepared in about 50% overall yield from diethyl malonate as follows:a: CH2=CH-CN, triton B (diox.); b: H3O+; c: EtOH, H+(C6H6); d: Na (tol.); e: HOCH2CH2OH, H+(C6H6); f: LiAlH4(THF); g: Collins (CH2Cl2). It is a colorless oil: ir (film) v 2700, 1725 and 1100–1030 cm−1; pmr (CCl4, 60 MHz) δ 3.90 (s,OCH2) and 9.57 (broad s,CH=O)

3. Regiospecific aldol condensations of the kinetic lithium enolates of methyl ketones

4. Compound4a, colorless oil; uv (EtOH) γmax228 nm (ε 10000); ir (film) v 1690 and 1655 (enone s-cis and s-trans conformations), 1620 and 1130–920 cm−1pmr (CCl4, 60 MHz) δ 0.90 (d, J = 6 Hz, (CH3)2CH), 3.93 (s,OCH2CH2O), 6.00 (d, J = 16 Hz, CH-CH=CH-CO) and 6.70 (dd, J1= 16 Hz, J2= 6 Hz, CH-CH[dbnd]CH-C[dbnd]O); ms (70 eV, rel. intensity) z/e 252 (4%), 169 (2%), 99 (92%) and 28 (100%). Compound4b, pale yellow oil; uv (EtOH) γmax260 nm (ε 12800); ir (film) v 1675, 1650, 1620, 1600 and 1100–1030 cm−1; pmr (CCl4, 60 MHz) δ 1.97 and 2.15 (2s, (CH3)2C[dbnd]CH), 3.95 (s,OCH2CH2O), 6.07 (d, J = 16 Hz, CH-CH[dbnd]CH-C[dbnd]O), 6.22 (broad s, (CH3)2C[dbnd]CH-C[dbnd]O) and 6.73 (dd, J1= 16 Hz, J2= 6 Hz, CH-CH[dbnd]CH-C[dbnd]O); ms (70 eV, rel. intensity) z/e 250 (2%), 206 (1%), 167 (2%), 99 (100%), 88 (45%) and 28 (85%)

5. Compound5a, colorless oil; ir (film) v 1710 and 1100–920 cm−1; pmr (CCl4, 60 MHz) δ 0.86 (d, J = 6 Hz, CH3-CH), 0.92 (d, J = 6 Hz, (CH3)2CH) and 3.90 (s,OCH2CH2O); ms (70 eV, rel. intensity) z/e 268 (8%), 183 (8%), 99 (100%), 86 (11%) and 69 (6%). Compound5b, colorless oil; uv (EtOH) γmax237 nm (ε 11400); ir (film) v 1695, 1630 and 1100–1030 cm−1; pmr (CCl4, 60 MHz) δ 0.83 (d, J = 6 Hz,CH3-CH), 1.83 and 2.09 (2s, (CH3)2C[dbnd]CH), 3.80 (s,OCH2CH2O) and 5.87 (broad s, C[dbnd]CH-C[dbnd]O)

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1. II. Monocyclic Sesquiterpenes;Total Synthesis of Natural Products;2007-02-20

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