Efficient Synthesis of Anhydrorhodovibrin and Analogues

Takeshi Yamada; Keiji Okada; Tetsuro Shinada; Yasufumi Ohfune; Hideki Hashimoto

doi:10.1055/s-0032-1317678

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(20): 2980-2984
DOI: 10.1055/s-0032-1317678

letter

Efficient Synthesis of Anhydrorhodovibrin and Analogues

Takeshi Yamada

^aOCARINA, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan

^bGraduate School of Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan Fax: +81(6)66053153 eMail: ohfune@sci.osaka-cu.ac.jp eMail: hassy@sci.osaka-cu.ac.jp

,

Keiji Okada

^aOCARINA, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan

^bGraduate School of Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan Fax: +81(6)66053153 eMail: ohfune@sci.osaka-cu.ac.jp eMail: hassy@sci.osaka-cu.ac.jp

^cCREST/JST, 4-1-8, Honcho, Kawaguchi, Saitama 332-0012, Japan

,

Tetsuro Shinada

^bGraduate School of Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan Fax: +81(6)66053153 eMail: ohfune@sci.osaka-cu.ac.jp eMail: hassy@sci.osaka-cu.ac.jp

,

Yasufumi Ohfune*

^bGraduate School of Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan Fax: +81(6)66053153 eMail: ohfune@sci.osaka-cu.ac.jp eMail: hassy@sci.osaka-cu.ac.jp

,

Hideki Hashimoto*

^aOCARINA, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan

^bGraduate School of Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan Fax: +81(6)66053153 eMail: ohfune@sci.osaka-cu.ac.jp eMail: hassy@sci.osaka-cu.ac.jp

^cCREST/JST, 4-1-8, Honcho, Kawaguchi, Saitama 332-0012, Japan

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Abstract

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Abstract

The synthesis of anhydrorhodovibrin and two analogues has been achieved in a highly efficient manner using a new Horner–Wadsworth–Emmons reagent bearing the Weinreb amide.

Key words

polyene - carotenoid - Horner–Wadsworth–Emmons reaction - Weinreb amide

Volltext

Referenzen

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15 NaH in THF, DBU with LiCl in MeCN, LDA in THF or NaNH₂ in CH₂Cl₂ did not affect the E/Z selectivity.
16 Geometrical isomers of 19 were separable by silica gel column chromatography. The Arbuzov reaction of (E)-19 and (Z)-19 gave (E)-8 and (Z)-8, respectively without any isomerization. The olefination of 13 with E-isomer 8 and Z-isomer 8 were examined, respectively, to provide a 1:3 mixture of 20.
17 The isomerization process to provide the E-conjugated double bond (C10 and C11) of 9 during the course of polyene chain elongation is interesting. We speculate that the isomerization could be triggered by means of the thermal isomerization. However, other possibilities such as photoisomerization and a base-catalyzed isomerization during the course of the HWE and Wittig reaction conditions as well as their complementary effects could not be ruled out.

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20 (R)-3: ¹H NMR (600 MHz, C₆D₆): δ = 6.60–6.79 (m, 5 H), 6.51 (d, J = 13.8 Hz, 1 H), 6.50 (d, J = 14.4 Hz, 1 H), 6.49 (d, J = 14.4 Hz, 1 H), 6.24–6.38 (m, 7 H), 5.91 (dt, J = 15.6, 7.2 Hz, 1 H), 5.75 (dt, J = 15.6, 7.2 Hz, 1 H), 5.24 (m, 1 H), 3.08 (s, 3 H), 2.32 (d, J = 7.2 Hz, 2 H), 2.20 (dt, J = 13.8, 7.2 Hz, 1 H), 1.97–2.15 (m, 3 H), 1.90 (s, 3 H), 1.89 (s, 3 H), 1.89 (s, 3 H), 1.88 (s, 6 H), 1.69 (s, 3 H), 1.60 (s, 3 H), 1.54–1.60 (m, 1 H), 1.44–1.51 (m, 1 H), 1.19–1.29 (m, 1 H), 1.10 (s, 6 H), 0.95 (d, J = 6.6 Hz, 3 H). ¹³C NMR (150 MHz, C₆D₆): δ = 138.5, 138.0, 137.9, 137.7, 136.9, 136.8, 136.7, 136.3, 135.7, 135.6, 133.6, 133.3, 133.1, 131.3, 131.0 (2 × C), 130.8, 130.6, 128.7, 128.3, 126.1, 125.6, 125.3, 125.2, 74.7, 49.1, 44.6, 41.1, 37.2, 33.4, 26.1, 25.8, 24.9, 19.7, 17.7, 13.1 (2 × C), 12.9 (2 × C), 12.8. HRMS (EI): m/z [M]⁺ calcd for [C₄₁H₆₀O]⁺: 568.4644; found: 568.4645; [α]_D ^25.1 +51.0 (c = 0.1, CHCl₃).
21 5: ¹H NMR (600 MHz, CDCl₃): δ = 6.55–6.66 (m, 4 H), 6.48 (dd, J = 15.0, 11.1 Hz, 1 H), 6.37 (d, J = 15.6 Hz, 1 H), 6.35 (d, J = 15.0 Hz, 1 H), 6.26 (d, J = 10.2 Hz, 1 H), 6.17–6.24 (3 H), 6.16 (d, J = 15.5 Hz, 1 H), 6.10 (d, J = 11.4 Hz, 1 H), 5.94 (d, J = 11.1 Hz, 1 H), 5.71 (dt, J = 15.5, 7.4 Hz, 1 H), 3.23 (s, 3 H), 2.32 (d, J = 7.4 Hz, 2 H), 1.98 (s, 3 H), 1.96 (s, 3 H), 1.94 (s, 3 H), 1.92 (s, 3 H), 1.82 (s, 3 H), 1.81 (s, 3 H), 1.15 (s, 6 H). ¹³C NMR (150 MHz, CDCl₃): δ = 137.9, 137.5 (2 × C), 136.6, 136.2, 136.1, 135.9, 135.2, 134.8, 133.0, 132.6, 131.4, 130.6, 130.3, 129.3, 126.0, 125.3, 125.1, 124.8, 124.6, 75.1, 49.3, 43.6, 26.3, 24.9, 18.6, 13.0, 12.9, 12.8 (2 × C). HRMS (FAB): m/z [M]⁺ calcd for [C₃₁H₄₄O]⁺: 432.3392; found: 432.3390.

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