Protecting-Group-Free Total
Synthesis of Goniothalesdiol A

Junpeng Li; Huaiji Zheng; Yingpeng Su; Xingang Xie; Xuegong She

doi:10.1055/s-0030-1258016

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Synlett 2010(15): 2283-2284
DOI: 10.1055/s-0030-1258016

LETTER

Protecting-Group-Free Total Synthesis of Goniothalesdiol A

Junpeng Li^a, Huaiji Zheng^a, Yingpeng Su^a, Xingang Xie*^a, Xuegong She*^a,b
^a State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
^b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: shexg@lzu.edu.cn;

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Publication History

Received 7 May 2010
Publication Date:
06 August 2010 (online)

Abstract
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Supplementary Material

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Abstract

A concise asymmetric total synthesis of goniothalesdiol A was accomplished using protecting-group-free strategy, in which silyl-Prins cyclization was used as the key step.

Key words

goniothalesdiol A - protecting-group-free - silyl-Prins cyclization - dihydroxylation

Supporting Information

References and Notes

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17

Goniothalesdiol A (1): powder; [α]_D ^²5 -21.0 (c = 0.2, CHCl₃). IR (KBr): 700, 758, 1047, 1078, 1170, 1203, 1438, 1735, 2920, 2952, 3425 cm^-¹. ^¹H NMR (400 MHz, CDCl₃): δ = 1.77 (td, J = 2.4, 14.0 Hz, 1 H), 1.94 (br s, 1 H), 2.08 (ddd, J = 2.0, 3.0, 14.0 Hz, 1 H), 2.47 (dd, J = 6.0, 15.2 Hz, 1 H), 2.59 (br s, 1 H), 2.63 (dd, J = 7.2, 15.2 Hz, 1 H), 3.53 (d, J = 9.6 Hz, 1 H), 3.66 (s, 3 H), 4.22 (d, J = 3.0 Hz, 1 H), 4.41 (m, 1 H), 4.55 (d, J = 9.6 Hz, 1 H), 7.31-7.41 (m, 5 H). ^¹³C NMR (100 MHz, CDCl₃): δ = 37.1, 40.5, 51.7, 67.1, 68.5, 72.7, 77.8, 127.4, 128.3, 128.6, 139.2, 171.3. HRMS (ESI): m/z [M + NH₄]⁺ calcd for C₁₄H₂₂NO₅: 284.1492; found: 284.1488.

Supplementary Material

Supporting Information