An Efficient Synthesis of (-)-Deacetylanisomycin Starting from d-Tyrosine [1]

Abstract

The antibiotic (-)-deacetylanisomycin was synthesized starting from d-tyrosine using Sharpless asymmetric dihydroxylation as a key reaction.

anisomycin - (-)-deacetylanisomycin - d-tyrosine - Sharpless asymmetric dihydroxylation

References

<A NAME="RZ06502SS-1">1</A>

IICT Communication Number: 4814.

<A NAME="RZ06502SS-2">2</A> Sobin BA. Tanner FW. J. Am. Chem. Soc.  1954,  76:  4053 

<A NAME="RZ06502SS-3">3</A> Schaefer JP. Wheatley PJ. J. Org. Chem.  1968,  33:  166 

<A NAME="RZ06502SS-4">4</A> Beereboom JJ. Butler K. Pennington FC. Solomons IA. J. Org. Chem.  1965,  30:  2334 

<A NAME="RZ06502SS-5">5</A> Wong CM. Can. J. Chem.  1968,  46:  1101 

<A NAME="RZ06502SS-6">6</A> Korzybski T. Kowsyk-Gindifer Z. Kurytowicz W. Antibiotics   Vol. 1:  American Society of Microbiology; Washington DC: 1978.  p.343-346  

<A NAME="RZ06502SS-7A">7a</A> Wong CM. Buccini J. Chang I. Te Raa J. Schwenk R. Can. J. Chem.  1969,  47:  2421 

<A NAME="RZ06502SS-7B">7b</A> Felner I. Schenker K. Helv. Chim. Acta  1970,  53:  754 

<A NAME="RZ06502SS-7C">7c</A> Verheyden JPH. Richardson AC. Bhatt RS. Grant BD. Fitch WL. Moffatt JG. Pure Appl. Chem.  1967,  50:  1363 

<A NAME="RZ06502SS-7D">7d</A> Buchanan JG. MacLean KA. Paulsen H. Wightman RH. J. Chem. Soc., Chem. Commun.  1983,  486 

<A NAME="RZ06502SS-8A">8a</A> Chandrasekhar S. Mohapatra S. Tetrahedron Lett.  1998,  39:  6415 

<A NAME="RZ06502SS-8B">8b</A> Chandrasekhar S. Mohapatra S. Yadav JS. Tetrahedron  1999,  55:  4763 

<A NAME="RZ06502SS-8C">8c</A> Chandrasekhar S. Reddy MV. Tetrahedron  2000,  56:  1111 

<A NAME="RZ06502SS-9">9</A> Hamada Y. Shibata M. Sugiura T. Kato S. Shioiri T. J. Org. Chem.  1987,  52:  1252 

<A NAME="RZ06502SS-10A">10a</A> Jurczak J. GoleBiowski A. Chem. Soc. Rev.  1989,  89:  149 

<A NAME="RZ06502SS-10B">10b</A> Hensel MJ. Fuchs PL. Synth. Commun.  1986,  16:  1285 

<A NAME="RZ06502SS-10C">10c</A> Davies SB. McKervey MA. Tetrahedron Lett.  1999,  40:  1229 

<A NAME="RZ06502SS-11A">11a</A> Sharpless KB. Amberg W. Bennani YL. Crispino GA. Hartung J. Jeong K.-S. Kwong H.-L. Morikawa K. Wang Z.-M. Xu D. Zhang X.-L. J. Org. Chem.  1992,  57:  2768 

<A NAME="RZ06502SS-11B">11b</A> Kolb HC. Andersson PG. Sharpless KB. J. Am. Chem. Soc.  1994,  116:  1278 

<A NAME="RZ06502SS-12">12</A> Reetz MT. Strack TJ. Mutulis F. Goddard R. Tetrahedron Lett.  1996,  37:  9293 

<A NAME="RZ06502SS-13">13</A>

No effort was made to isolate and characterize 7a, which was a minor constituent.

<A NAME="RZ06502SS-14">14</A> Baer HH. Zamkanei M. J. Org. Chem.  1988,  53:  4786