Stereoselectivity of Addition of Organometallic Reagents to Pentodialdo-1,4-furanoses: Synthesis of L-Axenose and D-Evermicose from a Common Intermediate

Giuliano, Robert M.; Villani, Frank J.

doi:10.1021/jo00106a035

Cited by 27 publications

(17 citation statements)

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“…The latter product was isomerized to the more stable methyl pyranosides 17 (methyl α- and β-axenoside) with methanolic HCl at 23 °C, a known transformation. 3b,20 Analytical data were in accord with those previously reported for methyl axenoside. 3 Selective O -acetylation of 17 provided methyl trioxacarcinoside A 18 (970 mg, 88% over two steps).…”

supporting

confidence: 80%

“…3b,20 Analytical data were in accord with those previously reported for methyl axenoside. 3 Selective O -acetylation of 17 provided methyl trioxacarcinoside A 18 (970 mg, 88% over two steps). Analytical data were in agreement with values reported for the same substance derived from natural sources.…”

supporting

confidence: 80%

“…2 Two prior synthetic routes to axenose have been published. 3,4 The first proceeded in 13 steps (1.6% yield) from l -fucose as starting material 3a and the second proceeded in 12 steps (~4% yield) from 2-deoxy- d -ribose as starting material. 3b Here we describe two different synthetic routes to the axenose–trioxacarcinose A carbohydrate class.…”

mentioning

confidence: 99%

“…3,4 The first proceeded in 13 steps (1.6% yield) from l -fucose as starting material 3a and the second proceeded in 12 steps (~4% yield) from 2-deoxy- d -ribose as starting material. 3b Here we describe two different synthetic routes to the axenose–trioxacarcinose A carbohydrate class. Both routes rely upon diastereoselective addition reactions of allylmetal reagents to α,β-dioxygenated ketones and employ the crystalline substance 4-phenylbenzyl (2 R ,3 S )-dihydroxybutyrate as starting material.…”

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confidence: 99%

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Diastereoselective Additions of Allylmetal Reagents to Free and Protected syn-α,β-Dihydroxyketones Enable Efficient Synthetic Routes to Methyl Trioxacarcinoside A

2012

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Two routes to the 2,6-dideoxysugar methyl trioxacarcinoside A are described. Each was enabled by an apparent α-chelation-controlled addition of an allylmetal reagent to a ketone substrate containing a free α-hydroxyl group and a β-hydroxyl substituent, either free or protected as the corresponding di-tert-butylmethyl silyl ether. Both routes provide practical access to gram-quantities of trioxacarcinose A in a form suitable for glycosidic coupling reactions.

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supporting

confidence: 80%

supporting

confidence: 80%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Diastereoselective Additions of Allylmetal Reagents to Free and Protected syn-α,β-Dihydroxyketones Enable Efficient Synthetic Routes to Methyl Trioxacarcinoside A

2012

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“…The naphthoquinone moiety was found to be derived biosynthetically from the shikimate pathway 90. The branched chain new sugar constituent of axenomycin B, L ‐axenose, has been synthesized 91…”

Section: New Antibioticsmentioning

confidence: 99%

Fifty Years of Chemical Research at Farmitalia

Arcamone¹

2009

Chemistry A European J

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This review contains a brief description of the chemistry developed in Farmitalia and, after 1978, Farmitalia-Carlo Erba Research Laboratories, during the second half of the last century. It gives an overview of work that represents a significant part of the chemistry carried out in Italy during this period in the field of medicinal and natural product chemistry. This is particularly true when we consider in addition to the work done intramurally in the said laboratories, the work done by academic scientists in the frame of the various extramural collaborations. Only a fraction of the chemical research actually carried out is reported here as time and space dictated a selection. Subjects typically associated with Farmitalia and which gave rise to important scientific or therapeutic outcomes are given preference in this review.

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