Synthesis of the Kedarcidin Core Structure by a Transannular Cyclization Pathway

Myers, Andrew G.; Goldberg, Steven D.

doi:10.1002/1521-3773(20000804)39:15<2732::aid-anie2732>3.0.co;2-9

Cited by 56 publications

(40 citation statements)

References 27 publications

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“…Reaction of cis-tetrahydrodiol 11b, under Myers' conditions, 15 failed to give any of the corresponding cyclic sulfate and only the trans-chlorohydrin 13b was isolated (71% yield). In this example, it was likely that the cyclic sulfate was slow to form and both the hydroxyl groups became chlorosulfonated to yield intermediate 14b which eventually led to the formation of chlorohydrin 13b, on warming the reaction mixture to room temperature followed by its aqueous workup.…”

Section: Resultsmentioning

confidence: 99%

Reactions of enantiopure cyclic diols with sulfuryl chloride

et al. 2014

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Monocyclic allylic cis-1,2-diols reacted with sulfuryl chloride at 0 °C in a regio- and stereo-selective manner to give 2-chloro-1-sulfochloridates, which were hydrolysed to yield the corresponding trans-1,2-chlorohydrins. At -78 °C, with very slow addition of sulfuryl chloride, cyclic sulfates were formed in good yields, proved to be very reactive with nucleophiles and rapidly decomposed on attempted storage. Reaction of a cyclic sulfate with sodium azide yielded a trans-azidohydrin without evidence of allylic rearrangement occurring. An enantiopure bicyclic cis-1,2-diol reacted with sulfuryl chloride to give, exclusively, a trans-1,2-dichloride enantiomer with retention of configuration at the benzylic centre and inversion at the non-benzylic centre; a mechanism is presented to rationalise the observation.

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Section: Resultsmentioning

confidence: 99%

Reactions of enantiopure cyclic diols with sulfuryl chloride

et al. 2014

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“…This compound can be made from the known enantiomerically pure lactone 7 13 in six steps after DIBAL-H reduction. Treatment of the resulting lactol with trimethylsilyl diazomethane enolate 14 gives the open chain alkyne. Overnight reaction in a mild basic methanolic media was required to isolate 8 in 39% overall yield.…”

Section: Synthesis Of the Estermentioning

confidence: 93%

Diastereoselective Access to the Spirotetronate Subunit of the Quartromicins

Bedel¹,

Français²,

Haudrechy³

2005

Synlett

13
0
9
0

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Diastereoselective Access to the Spirotetronate Subunit of the Quartromicins D i a s t e r e o s e l e c t i v e A c c e s s t o t h e S p i r o t e t r o n a t e S u b u n i t o f t h e Q u a r t r o m i c i n sAbstract: The agalacto-spirotetronate B subunit of quartromicins was synthesized in a predictible manner, following the ClaisenIreland/metathesis approach (CIM strategy). Ene-yne ring-closure and selective mismatch Sharpless dihydroxylation are discussed as key steps, allowing an efficient approach to these structures.

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“…In Myers' synthesis of the Kedarcidin core structure, this method is used to convert lactol 13 to acetylene 14 in 81% yield. 17 In Furstner's approach to Hikizimycin, mannofuranose 15 is submitted to the Colvin rearrangement and yields 57% of terminal alkyne 16 and 12% of its C-silylated analogue. The latter is easily desilylated to furnish alkyne 16 in 65% yield overall.…”

Section: Broadening the Scope Of The Reactionmentioning
confidence: 99%

Conversion of carbonyl compounds to alkynes: general overview and recent developments
Habrant
¹
,
Rauhala
²
,
Koskinen
³

2010
Chem. Soc. Rev.
141
0
91
0
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Synthesis of the Kedarcidin Core Structure by a Transannular Cyclization Pathway

Cited by 56 publications

References 27 publications

Reactions of enantiopure cyclic diols with sulfuryl chloride

Reactions of enantiopure cyclic diols with sulfuryl chloride

Diastereoselective Access to the Spirotetronate Subunit of the Quartromicins

Conversion of carbonyl compounds to alkynes: general overview and recent developments

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