It takes the average reader 5 hours and 49 minutes to read Strategies and Tactics in Organic Synthesis by Michael F. Greaney
Assuming a reading speed of 250 words per minute. Learn more
This chapter describes the synthesis of two related sesquiterpenes, anislactone A and merrilactone A. We initially accessed a tetracyclic oxetane in the merrilactone series using a Paternò–Büchi reaction but found the compound to be too underfunctionalized to advance further. We then developed an approach based on reductive epoxide ring opening, whereby a fully elaborated C-ring epoxy-cyclopentane, containing five stereocenters, could undergo reductive epoxide cleavage when treated with Ti(III). The resulting tertiary radical then participates in a 5-exo-dig cyclization onto a pendant alkyne to afford the complete carbon skeleton of both natural products. From this point, orthogonal functionalization routes enabled the synthesis of both anislactone A and merrilactone A. A second-generation merrilactone A synthesis is then described, growing out of discoveries made over the course of the first route in the area of cyclopentannulation. An iodo-aldol method was used to develop an approach to the anislactone skeleton and succeeded in producing the BC bicycle with good stereocontrol and functional group tolerance. Further functionalization, however, did not prove possible due to excessive steric hindrance around the incorporated iodo group preventing any productive transformation. This problem was solved by switching the nucleophile in the tandem-aldol process to cyanide. The resulting domino cyanide-addition aldol cyclization was then successfully employed in the formal synthesis of merrilactone A, using a late-stage [2+2] photocycloaddition to access the D-ring.
Strategies and Tactics in Organic Synthesis by Michael F. Greaney is 344 pages long, and a total of 87,376 words.
This makes it 116% the length of the average book. It also has 107% more words than the average book.
The average oral reading speed is 183 words per minute. This means it takes 7 hours and 57 minutes to read Strategies and Tactics in Organic Synthesis aloud.
Strategies and Tactics in Organic Synthesis is suitable for students ages 12 and up.
Note that there may be other factors that effect this rating besides length that are not factored in on this page. This may include things like complex language or sensitive topics not suitable for students of certain ages.
When deciding what to show young students always use your best judgement and consult a professional.
Strategies and Tactics in Organic Synthesis by Michael F. Greaney is sold by several retailers and bookshops. However, Read Time works with Amazon to provide an easier way to purchase books.
To buy Strategies and Tactics in Organic Synthesis by Michael F. Greaney on Amazon click the button below.
Buy Strategies and Tactics in Organic Synthesis on Amazon