14 research outputs found
Concise and Stereocontrolled Synthesis of the Tetracyclic Core of Daphniglaucin C
The tetracyclic core of daphniglaucin C was prepared from the known 4-keto-<i>N</i>-Boc methyl-l-prolinate in 15 steps with a cumulative yield of 14.7%. The key steps toward this core motif feature a reductive double bond transposition from an unactivated tertiary allylic alcohol, a Pd-catalyzed Stille coupling, and Dieckmann cyclizations
Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
This article describes synthetic studies that culminated
in the
first total synthesis of pactamycin and pactamycate and, in parallel,
the two known congeners, de-6-MSA-pactamycin and de-6-MSA-pactamycate,
lacking the 6-methylsalicylyl moiety. Starting with l-threonine
as a <i>chiron</i>, a series of stereocontrolled condensations
led to a key cyclopentenone harboring a spirocyclic oxazoline. A series
of systematic functionalizations led initially to the incorrect cyclopentanone
epoxide, which was “inverted” under solvolytic conditions.
Installation of the remaining groups and manipulation of the oxazoline
eventually led to pactamycin, pactamycate, and their desalicylyl analogues
Synthesis of a Model Tetracyclic Core Structure of Calyciphylline B‑Type Alkaloids
Herein,
we report the enantioselective synthesis of a functionalized
aza-octahydropentalene and its elaboration to a model tetracyclic
core structure of calyciphylline B-type alkaloids
Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
This article describes synthetic studies that culminated
in the
first total synthesis of pactamycin and pactamycate and, in parallel,
the two known congeners, de-6-MSA-pactamycin and de-6-MSA-pactamycate,
lacking the 6-methylsalicylyl moiety. Starting with l-threonine
as a <i>chiron</i>, a series of stereocontrolled condensations
led to a key cyclopentenone harboring a spirocyclic oxazoline. A series
of systematic functionalizations led initially to the incorrect cyclopentanone
epoxide, which was “inverted” under solvolytic conditions.
Installation of the remaining groups and manipulation of the oxazoline
eventually led to pactamycin, pactamycate, and their desalicylyl analogues
Species Plantarum
Verso originally left blank for additional notes. Notes made level with related material on facing page
Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
This article describes synthetic studies that culminated
in the
first total synthesis of pactamycin and pactamycate and, in parallel,
the two known congeners, de-6-MSA-pactamycin and de-6-MSA-pactamycate,
lacking the 6-methylsalicylyl moiety. Starting with l-threonine
as a <i>chiron</i>, a series of stereocontrolled condensations
led to a key cyclopentenone harboring a spirocyclic oxazoline. A series
of systematic functionalizations led initially to the incorrect cyclopentanone
epoxide, which was “inverted” under solvolytic conditions.
Installation of the remaining groups and manipulation of the oxazoline
eventually led to pactamycin, pactamycate, and their desalicylyl analogues
Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
This article describes synthetic studies that culminated
in the
first total synthesis of pactamycin and pactamycate and, in parallel,
the two known congeners, de-6-MSA-pactamycin and de-6-MSA-pactamycate,
lacking the 6-methylsalicylyl moiety. Starting with l-threonine
as a <i>chiron</i>, a series of stereocontrolled condensations
led to a key cyclopentenone harboring a spirocyclic oxazoline. A series
of systematic functionalizations led initially to the incorrect cyclopentanone
epoxide, which was “inverted” under solvolytic conditions.
Installation of the remaining groups and manipulation of the oxazoline
eventually led to pactamycin, pactamycate, and their desalicylyl analogues
Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
This article describes synthetic studies that culminated
in the
first total synthesis of pactamycin and pactamycate and, in parallel,
the two known congeners, de-6-MSA-pactamycin and de-6-MSA-pactamycate,
lacking the 6-methylsalicylyl moiety. Starting with l-threonine
as a <i>chiron</i>, a series of stereocontrolled condensations
led to a key cyclopentenone harboring a spirocyclic oxazoline. A series
of systematic functionalizations led initially to the incorrect cyclopentanone
epoxide, which was “inverted” under solvolytic conditions.
Installation of the remaining groups and manipulation of the oxazoline
eventually led to pactamycin, pactamycate, and their desalicylyl analogues
Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
This article describes synthetic studies that culminated
in the
first total synthesis of pactamycin and pactamycate and, in parallel,
the two known congeners, de-6-MSA-pactamycin and de-6-MSA-pactamycate,
lacking the 6-methylsalicylyl moiety. Starting with l-threonine
as a <i>chiron</i>, a series of stereocontrolled condensations
led to a key cyclopentenone harboring a spirocyclic oxazoline. A series
of systematic functionalizations led initially to the incorrect cyclopentanone
epoxide, which was “inverted” under solvolytic conditions.
Installation of the remaining groups and manipulation of the oxazoline
eventually led to pactamycin, pactamycate, and their desalicylyl analogues
Total Synthesis of Pactamycin and Pactamycate: A Detailed Account
This article describes synthetic studies that culminated
in the
first total synthesis of pactamycin and pactamycate and, in parallel,
the two known congeners, de-6-MSA-pactamycin and de-6-MSA-pactamycate,
lacking the 6-methylsalicylyl moiety. Starting with l-threonine
as a <i>chiron</i>, a series of stereocontrolled condensations
led to a key cyclopentenone harboring a spirocyclic oxazoline. A series
of systematic functionalizations led initially to the incorrect cyclopentanone
epoxide, which was “inverted” under solvolytic conditions.
Installation of the remaining groups and manipulation of the oxazoline
eventually led to pactamycin, pactamycate, and their desalicylyl analogues