A Total Synthesis of (±)-Zoapatanol and Demethyl-ORF13811

Kocieński, Philip; Love, Christopher J.; J, Whitby Richard; Costello, Gerard; Roberts, David A.

doi:10.1016/s0040-4020(01)89243-7

Cited by 63 publications

(27 citation statements)

References 25 publications

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“…Excellent chemoselectivity toward alkynes in the presence of other isolated olefins was also achieved by Kociensky. 228 2.2.1.2. In Situ Generated Hydrogen Gas.…”

Section: Homogeneous Catalystsmentioning

confidence: 99%

Are Alkyne Reductions Chemo-, Regio-, and Stereoselective Enough To Provide Pure (Z)-Olefins in Polyfunctionalized Bioactive Molecules?

et al. 2012

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“…Excellent chemoselectivity toward alkynes in the presence of other isolated olefins was also achieved by Kociensky. 228 2.2.1.2. In Situ Generated Hydrogen Gas.…”

Section: Homogeneous Catalystsmentioning

confidence: 99%

Are Alkyne Reductions Chemo-, Regio-, and Stereoselective Enough To Provide Pure (Z)-Olefins in Polyfunctionalized Bioactive Molecules?

et al. 2012

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“…[35] The regioselectivity pattern of this method, which has been applied in a total synthesis, [36] appears to be very different from our own.…”

Section: Comparison With Other Methods: Advantages and Drawbacksmentioning

confidence: 57%

Titanium‐Mediated Carboxylation of Alkynes With Carbon Dioxide

Six

2003

Eur J Org Chem

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The regioselective carboxylation of nonactivated internal alkynes can be performed with carbon dioxide under atmospheric pressure using a simple procedure based on the chemistry of Sato‐type diisopropyloxytitanacyclopropenes. Various polysubstituted vinylcarboxylic acids and butenolides can be prepared in this way. In addition, this paper describes an experimental protocol for the preparation of solutions of (η2‐cyclopentene)diisopropyloxytitanium. This complex also reacts with carbon dioxide, and mediates pinacol coupling of acetophenone. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…Other than alkenyl and methoxymethyl substituted epoxides, most of the work on 7- endo -selective epoxide opening has been done on trisubstituted epoxides featuring a directing methyl group. Early examples have shown that acid-catalyzed cyclizations of appropriately substituted trialkyl epoxides can produce oxepanes in good yield [ 138 – 141 ]. The systematic studies of directing effects of methyl substituents and their application in the synthesis of polyoxepanes via epoxide-opening cascades were reported by the McDonald group [ 142 , 143 ].…”

Section: Construction Of Oxepanes Via Endo -Selmentioning

confidence: 99%

Synthesis of Marine Polycyclic Polyethers via Endo-Selective Epoxide-Opening Cascades

Vilotijević

Jamison

2010

Marine Drugs

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The proposed biosynthetic pathways to ladder polyethers of polyketide origin and oxasqualenoids of terpenoid origin share a dramatic epoxide-opening cascade as a key step. Polycyclic structures generated in these biosynthetic pathways display biological effects ranging from potentially therapeutic properties to extreme lethality. Much of the structural complexity of ladder polyether and oxasqualenoid natural products can be traced to these hypothesized cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of ladder polyethers and oxasqualenoid natural products.

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A Total Synthesis of (±)-Zoapatanol and Demethyl-ORF13811

Cited by 63 publications

References 25 publications

Are Alkyne Reductions Chemo-, Regio-, and Stereoselective Enough To Provide Pure (Z)-Olefins in Polyfunctionalized Bioactive Molecules?

Are Alkyne Reductions Chemo-, Regio-, and Stereoselective Enough To Provide Pure (Z)-Olefins in Polyfunctionalized Bioactive Molecules?

Titanium‐Mediated Carboxylation of Alkynes With Carbon Dioxide

Synthesis of Marine Polycyclic Polyethers via Endo-Selective Epoxide-Opening Cascades

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