Enantioselective Synthesis of Pseudomonic Acids. I. Synthesis of Key Intermediates

Schönenberger, Bernhard; Summermatter, Walter; Ganter, C.

doi:10.1002/hlca.19820650739

Cited by 19 publications

(2 citation statements)

References 10 publications

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“…Schonenberger reported the first enantioselective synthesis of pseudomonic acid precursors from carbohydrate starting materials (Scheme 5). 46 The elaboration of D-ribose is particularly useful in the synthesis of pseudomonic acid B (2) and its derivatives since the chiral intermediates in this strategy contain a hydroxyl group at C-8 of the pyran. Because D-ribose already contains the requisite C-6 and C-7 hydroxyl groups, Schonenberger's primary concern was introduction of the C-5 and C-8 side chains.…”

Section: B the Schdnenberger Synthesismentioning

confidence: 99%

The Pseudomonic Acids

Class¹,

DeShong²

1995

Chem. Rev.

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Yvonne J. Class (right) obtained her B.Sc. in Chemistry at The Pennsylvania State University where she performed research with Lloyd Jackman. She received her Ph.D. in Organic Chemistry in 1995 from the University of Maryland under the supervision ol Philip DeShong.Philip DeShong (left) was born in Texas in 1949 and received his undergraduate education at the College of William and Mary and the University of Texas at Austin (B.Sc. in 1971). While at Texas, Royston M. Roberts and Philip Stotter supervised his research training. He obtained his Sc.D. from the Massachusetts Institute of Technology in 1976 studying with George H, Buchi. After postdoctoral studies with Duilio Arigoni at the Eidgenossische Technische Hochschule, Zurich (1976-1979 and Chris Walsh at MIT (1979), he accepted a faculty position at The Pennsylvania State University. In 1986, he moved to the University of Maryland where he is Professor of Chemistry.

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Section: B the Schdnenberger Synthesismentioning

confidence: 99%

The Pseudomonic Acids

Class¹,

DeShong²

1995

Chem. Rev.

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“…To construct a 2,3,4,5-tetrasubstituted pyran ring system, alcohol 11 was treated with 3 equiv of sodium hexamethyldisilazide at −78 °C in THF, affording two cyclization products 12 and 13 as a mixture of diastereoisomers at the 2-position, where β-elimination of the benzyloxy group, followed by Michael addition of the primary alcohol to the resulting α,β-unsaturated ester, took place simultaneously …”

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confidence: 99%