1997
DOI: 10.1039/cs9972600387
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Approaches to the synthesis of ingenol

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Cited by 63 publications
(34 citation statements)
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“…Brilliant use of olefin metathesis reactions in a complex setting was made by Wood and co‐workers in their recent total synthesis of ingenol ( 16 , Scheme ) 42. The parent member of a large class of ingenane diterpenes, ingenol ( 16 ) has captivated the attention of synthetic chemists for more than 20 years 43. The irresistible lure of this natural product is due partly to its promising biological activity,44 but also to its rather remarkable polycyclic, highly oxygenated molecular architecture, the most distinctive feature of which is the strained “inside–outside” ( trans ) intrabridgehead stereochemistry of the bicyclic BC‐ring system 45.…”
Section: The Alkene‐metathesis Reactionmentioning
confidence: 68%
“…Brilliant use of olefin metathesis reactions in a complex setting was made by Wood and co‐workers in their recent total synthesis of ingenol ( 16 , Scheme ) 42. The parent member of a large class of ingenane diterpenes, ingenol ( 16 ) has captivated the attention of synthetic chemists for more than 20 years 43. The irresistible lure of this natural product is due partly to its promising biological activity,44 but also to its rather remarkable polycyclic, highly oxygenated molecular architecture, the most distinctive feature of which is the strained “inside–outside” ( trans ) intrabridgehead stereochemistry of the bicyclic BC‐ring system 45.…”
Section: The Alkene‐metathesis Reactionmentioning
confidence: 68%
“…In 1997, Kim and Winkler surveyed the approaches that have been examined in various laboratories with the goal of the synthesis of ingenanes 129. The published approaches included inter‐ and intramolecular [6 + 4] cycloadditions of tropones to dienes, intramolecular [4 + 3] cycloadditions of cyclic oxyallyls to a tethered furan, Lewis‐acid‐catalysed aldol cyclization, photoinduced ring expansion/ring contraction, a ring contraction strategy based on the Ireland–Claisen rearrangement, and transformation of an out–out system to an in–out isomer by [1,5]‐hydrogen sigmatropic rearrangement and intramolecular dioxenone photocycloaddition and fragmentation.…”
Section: Ingenol 3‐angelate (Picato®)mentioning
confidence: 99%
“…Ingenol mebutate (picato; Figure 1) was recently approved by the FDA as a first‐in‐class drug for the topical treatment of actinic keratosis, a precancerous skin condition 6. Consequently, some elegant synthetic strategies for the formation of bridged seven‐membered‐ring systems have been developed,1g,h, 2e including rearrangement,1d,f, 4f fragmentation,1c, 4e ring‐closing metathesis,1e and intramolecular cyclizations 2c,d. 3c However, so far no general reactions are available for the direct and efficient synthesis of bridged cycloheptane bicyclic systems.…”
Section: Methodsmentioning
confidence: 99%