Synthesis of C13–C22 of amphidinolide T2 via nickel-catalyzed reductive coupling of an alkyne and a terminal epoxide

O’Brien, Karen C.; Colby, Elizabeth A.; Jamison, Timothy F.

doi:10.1016/j.tet.2005.03.116

Cited by 28 publications

(3 citation statements)

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“…(167)) [330]. A related reductive coupling of an alkyne and an epoxide was used in a synthesis toward amphidinolide T2 [908]. Nickel catalyzed asymmetric reductive couplings of 1,3-enynes with ketones to give 5-hydroxy-1,3-dienes [909].…”

Section: Formation Of Carbon-carbon and -Nitrogen Bonds From Carbonylmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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Section: Formation Of Carbon-carbon and -Nitrogen Bonds From Carbonylmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…Among the advantages of the hydrolytic KR process are its broad applicability over a range of simple as well as functionalized terminal epoxides, high enantioselectivity, remarkable practical appeal, and low catalyst loading. Unsurprisingly, the generality and broad substrate specificity of Jacobsen’s hydrolytic KR methodology has been exploited for the production of a wide range of chiral synthons for natural products and bioactive compounds synthesis, including recent strategies directed towards the synthesis of cytochalasin B,122 apicularen A,123 ( S )‐timolol,124 decarestrictine D,125 cryptocarya diacetate,126 (2 S ,3 R )‐4‐hydroxyornithine,127 (+)‐negamycin,128 (−)‐ cis ‐lauthisan and (+)‐isolaurepan,129 herbarumin III,130 (−)‐deoxoprosopinine,131 ( S )‐atenolol,132 tarchonanthuslactone,133 aspinolide A,134 massoialactone,135 ( R )‐tuberculostearic acid,136 dihydrobenzofurans,137 ( S )‐vigabatrin and ( S )‐dihydrokavain,138 1‐deoxy‐5‐hydroxyshingosine analogues,139 (+)‐patulolide C,140 (+)‐bataxolol,141 (+)‐diplodialides , B and C,142 ( R )‐mexiletine,143 (+)‐allosedamine,144 ( S )‐metoprolol and ( S )‐betaxolol,145 enciprazine,146 and C 13 –C 22 of amphidinolide T2,147 amphidinolide T1,148 iso ‐cladospolide B and cladospolide B,149 anti‐inflammatory agent (7 S ,17 S )‐resolvin D5,150 ( S )‐ and ( R )‐naftopidil,151 neocarazostatin,152 nonactin,153 elecanacin,154 (+)‐peloruside,155 spongiacysteine,156 astrocyte activation suppressor ONO‐2506,157 (−)‐indolizidine 223AB,158 (7 S ,16 R ‐17S)‐resolvin D2,159 (−)‐galantinic acid,160 (+)‐Sch 642305,161 (4 R )‐hydroxy analogues of Annonaceous acetogenins,162 insect pheromones,163 hNK‐1 receptor antagonist,164 L ‐carnitine,165 and (+)‐brefeldin A 166. The use and range of chiral epoxides resolved in these natural or bioactive product syntheses clearly stands as a testament to the true power of Jacobsen’s hydrolytic KR as a routine methodology for stereoselective organic synthesis, as shown in Figure 5.…”

Section: Kinetic Resolution Of Epoxidesmentioning

confidence: 99%

Catalytic Non‐Enzymatic Kinetic Resolution

Pellissier

2011

Adv Synth Catal

311

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While tremendous advances have been made in asymmetric synthesis, the resolution of racemates is still the most important industrial approach to the synthesis of chiral compounds. The use of enzymes for the kinetic resolution (KR) of racemic substrates to afford enantiopure compounds in high enantioselectivity and good yield has long been a popular strategy in synthesis. However, transition metal-mediated and more recently organocatalyzed KRs have gained popularity within the synthetic community over the last two decades due to the progress made in the development of chiral catalysts for asymmetric reactions. Many catalytic non-enzymatic procedures have been developed providing high enantioselectivity and yield for both products and recovered starting materials. Indeed, the non-enzymatic KR of racemic compounds based on the use of a chiral catalyst is presently an area of great importance in asymmetric organic synthesis. The goal of this review is to provide an update on the principal developments of catalytic non-enzymatic KR covering the literature since 2004. This review is subdivided into seven sections, according to the different types of compounds that have been resolved through catalytic non-enzymatic KR, such as alcohols,

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“…Jamison and Colby have also reviewed in a comparative fashion the synthesis of T-series amphidinolides, 60 and described a route to the C13-C22 domain of amphidinolide T2. 61 In other studies on the amphidinolides, a concise synthesis of the C9-C26 fragment of amphidinolide B 1 62 has been accomplished by Carter and Zhang. 63 The synthesis features a straightforward elimination approach to the C13-C15 diene.…”

Section: Amphidinolidesmentioning

confidence: 99%