SYNTHESIS OF AMERICANIN-D

By regioselective self-coupling with silver oxide as oxidant the 2,3-trans-2-phenylbenzofuran 8 was synthesized in good yield. Reduction of 8 led in an unambiguous way to americanin-D (rac-1). Synthetic and natural product were identical in every respect.

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Published inLiebigs Annalen der Chemie no. 4; pp. 357 - 360
Main Authors ANTUS, S, BAUER, R, GOTTSEGEN, A, SELIGMANN, O, WAGNER, H
Format Journal Article
LanguageGerman
Published DEERFIELD BEACH Wiley 01.04.1987
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Abstract By regioselective self-coupling with silver oxide as oxidant the 2,3-trans-2-phenylbenzofuran 8 was synthesized in good yield. Reduction of 8 led in an unambiguous way to americanin-D (rac-1). Synthetic and natural product were identical in every respect.
AbstractList By regioselective self-coupling with silver oxide as oxidant the 2,3-trans-2-phenylbenzofuran 8 was synthesized in good yield. Reduction of 8 led in an unambiguous way to americanin-D (rac-1). Synthetic and natural product were identical in every respect.
Author WAGNER, H
SELIGMANN, O
ANTUS, S
GOTTSEGEN, A
BAUER, R
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References FREUDENBERG K (WOS:A1987H277300013.5) 1952; 12
MERLINI, L (WOS:A1980JK76600024) 1980
WAGNER, H (WOS:A1971J394100003) 1971
ANTUS, S (WOS:A1986C219500006) 1986
WEISSMAN, PM (WOS:A19667184500063) 1966; 31
WOO, WS (WOS:A1978FL37700015) 1978
WOO, WS (WOS:A1980KP82300010) 1980; 21
WINTERFELDT, E (WOS:A1975AS93600001) 1975
ARNOLDI, A (WOS:A1984SX14400015) 1984; 22
FIEBIG M (BCI:BCI198579036181) 1984; 51
DAVIDSON, RS (WOS:A19644233B00065) 1964
References_xml – start-page: 647
  year: 1986
  ident: WOS:A1986C219500006
  article-title: THE DEFINITE STRUCTURE OF AMERICANIN-A AND HYDNOCARPIN
  publication-title: LIEBIGS ANNALEN DER CHEMIE
  contributor:
    fullname: ANTUS, S
– start-page: 1895
  year: 1971
  ident: WOS:A1971J394100003
  article-title: STRUCTURE OF SILYCHRISTINE, SECOND SILYMARINE ISOMER FROM SILYBUM-MARIANUM
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: WAGNER, H
– volume: 21
  start-page: 4255
  year: 1980
  ident: WOS:A1980KP82300010
  article-title: THE STRUCTURE OF NEW LIGNANS FROM THE SEEDS OF PHYTOLACCA AMERICANA
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: WOO, WS
– start-page: 4907
  year: 1964
  ident: WOS:A19644233B00065
  article-title: CALCIFEROL + ITS RELATIVES .6. DEGRADATION OF 7-OXOCHOLESTERYL ACETATE TO SOME DES-AB-CHOLESTANE DERIVATIVES
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY
  contributor:
    fullname: DAVIDSON, RS
– volume: 22
  start-page: 1537
  year: 1984
  ident: WOS:A1984SX14400015
  article-title: SYNTHESIS OF THE NATURAL COUMARINOLIGNOIDS PROPACIN AND CLEOMISCOSIN-A AND CLEOMISCOSIN-B - AN EMPIRICAL SPECTROSCOPIC METHOD TO DISTINGUISH REGIOISOMERS OF NATURAL BENZODIOXANE LIGNOIDS
  publication-title: HETEROCYCLES
  contributor:
    fullname: ARNOLDI, A
– volume: 12
  start-page: 1181
  year: 1952
  ident: WOS:A1987H277300013.5
  publication-title: LIEBIGS ANN CHEM
  contributor:
    fullname: FREUDENBERG K
– volume: 31
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  year: 1966
  ident: WOS:A19667184500063
  article-title: SELECTIVE REDUCTIONS .6. REACTION OF LITHIUM TRI-T-BUTOXYALUMINOHYDRIDE WITH PHENOLIC ESTERS . A NEW ALDEHYDE SYNTHESIS
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: WEISSMAN, PM
– start-page: 775
  year: 1980
  ident: WOS:A1980JK76600024
  article-title: BENZODIOXANS BY OXIDATIVE PHENOL COUPLING - SYNTHESIS OF SILYBIN
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
  contributor:
    fullname: MERLINI, L
– start-page: 3239
  year: 1978
  ident: WOS:A1978FL37700015
  article-title: STRUCTURE OF AMERICANINE, NEW NEOLIGNANE FROM PHYTOLACCA-AMERICANA
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: WOO, WS
– start-page: 617
  year: 1975
  ident: WOS:A1975AS93600001
  article-title: APPLICATIONS OF DIISOBUTYLALUMINUM HYDRIDE (DIBAH) AND TRIISOBUTYLALUMINUM (TIBA) AS REDUCING AGENTS IN ORGANIC SYNTHESIS
  publication-title: SYNTHESIS-STUTTGART
  contributor:
    fullname: WINTERFELDT, E
– volume: 51
  start-page: 310
  year: 1984
  ident: BCI:BCI198579036181
  article-title: NEW ANTIHEPATOTOXICALLY ACTIVE FLAVONOLIGNANS FROM A WHITE-FLOWERING VARIETY OF SILYBUM
  publication-title: Planta Medica
  contributor:
    fullname: FIEBIG M
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Snippet By regioselective self-coupling with silver oxide as oxidant the 2,3-trans-2-phenylbenzofuran 8 was synthesized in good yield. Reduction of 8 led in an...
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Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Title SYNTHESIS OF AMERICANIN-D
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