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DOI: 10.1055/s-2007-984497
A Formal Stereoselective Synthesis of (-)-Maurenone
Publication History
Publication Date:
25 June 2007 (online)
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Abstract
An efficient formal synthesis of marine polypropionate (-)-maurenone is described. Highlights of the strategy include the utilization of a desymmetrization technique and the activation of the epoxide oxygen with a silyl triflate followed by intramolecular hydride transfer - a novel transformation.
Key words
desymmetrization - Sharpless asymmetric epoxidation - polyketide
- 1
Manker DC.Faulkner DJ.Xe CF.Clardy J. J. Org. Chem. 1986, 51: 814 - 2
Davies-Colman MT.Garson MJ. Nat. Prod. Rep. 1998, 15: 477 - 3
Roll DM.Biskupiak JE.Mayne CL.Ireland CM. J. Am. Chem. Soc. 1986, 108: 6680 - 4
Hochlowski JE.Faulkner DJ.Matsumoto GK.Clardy J. J. Am. Chem. Soc. 1983, 105: 74 -
5a
Garson MJ.Goodman JM.Paterson I. Tetrahedron Lett. 1994, 35: 6929 -
5b
Garson MJ. Chem. Rev. 1993, 93: 1699 -
5c
Manker DC.Garson MJ.Faulkner DJ. J. Chem. Soc., Chem. Commun. 1988, 1061 -
5d
Garson MJ.Jones DD.Small CJ.Liang J.Clardy J. Tetrahedron Lett. 1994, 35: 6921 - 6
Crossman JS.Perkins MV. J. Org. Chem. 2006, 71: 117 - 7
Chakraborty TK.Tapadar S. Tetrahedron Lett. 2003, 44: 2541 - 8
Jung ME.D’Amico DC. J. Am. Chem. Soc. 1993, 115: 12208 - 9
Yadav JS.Rao CS.Chandrasekhar S.Ramarao AV. Tetrahedron Lett. 1995, 36: 7717 - 10
Yadav JS.Abraham S.Reddy M.Sabitha G.Sankar AR.Kunwar AC. Tetrahedron Lett. 2001, 42: 4713 - 11
Yadav JS.Ahmed M. Tetrahedron Lett. 2002, 43: 7147 - 12
Yadav JS.Reddy KB.Sabitha G. Tetrahedron Lett. 2004, 45: 6475 - 13
Yadav JS.Srinivas R.Sathaiah K. Tetrahedron Lett. 2006, 47: 1603 - 14
Yadav JS.Reddy PV.Chandraiah L. Tetrahedron Lett. 2007, 48: 145
References and Notes
The spectral and physical data of aldehyde 3 and ketone 4 matched in all respects with reported data (ref. 6).
Selected Physical Data
Compound 3: clear oil; R
f
= 0.43 (Et2O-hexane, 10:90); [α]D
20 +51.6 (c 1.0 CHCl3).
[6]
Compound 4: colorless oil; R
f
= 0.50 (EtOAc-hexane, 10:90); [α]D
20 +30.5 (c 1.0 CHCl3).
[6]
Compound 5: colorless oil; R
f
= 0.40 (EtOAc-hexane, 10:90); [α]D
20 +19.4 (c 1.0 CHCl3). 1H NMR (300 MHz, CDCl3): δ = 3.65 (dd, 1 H, J = 12.0, 4.5 Hz), 3.53 (dd, 1 H, J = 12.0, 8.3 Hz), 2.95 (t, 1 H, J = 6.0 Hz), 1.95 (dd, 1 H, J = 8.3, 5.3 Hz), 1.55 (m, 2 H), 1.29 (s, 3 H), 1.05 (t, 3 H, J = 7.5 Hz). 13C NMR (75 MHz, CDCl3): δ = 65.6, 61.4, 61.1, 21.4, 13.9, 10.3. LC-MS: m/z = 117 [M + H]+.
Compound 16: colorless oil; R
f
= 0.50 (EtOAc-hexane, 10:90); [α]D
20 +42.20 (c 2.0 CHCl3). 1H NMR (300 MHz, CDCl3): δ = 7.25 (m, 5 H), 4.40 (Abq, 2 H), 3.55 (dd, 1 H, J = 6.0, 3.0 Hz), 2.90 (m, 1 H), 2.50 (m, 2 H), 1.58 (m, 2 H), 1.30 (m, 1 H), 1.00 (m, 12 H). 13C NMR (75 MHz, CDCl3): δ = 214.9, 138.9, 128.1, 127.4, 127.3, 86.6, 74.4, 48.0, 37.0, 36.9, 23.3, 16.4, 13.8, 12.1, 7.5. HRMS: m/z calcd for C17H26O2Na [M + Na+]: 285.1820; found: 285.1823.